Chapter

An Overview of N-Heterocyclic
Carbene: Properties and Applications
Norein Sakander, Ajaz Ahmed, Bisma Rasool
and Debaraj Mukherjee

Abstract

In 1991, N-heterocyclic carbenes were isolated and characterised successful

introduced an entirely new class of organic compounds for research. From these
origin as scientific curiosities, N-heterocyclic carbenes today rank among organic
chemistry’s most powerful tool, having a wide applicability in commercially impor-
tant processes. In this chapter, we summarise the general properties and uses of
N-heterocyclic carbenes in modern chemistry and demonstrates how these proper-
ties are being exploited.

Keywords: N-heterocyclic carbene, asymmetric catalysis, umpolung, organocatalysis,

coordination chemistry

1. Introduction

Carbenes, a fascinating family of carbon-containing compounds, are described

as neutral compounds having a divalent carbon atom with a six-electron valence
shell. Nevertheless, unbound carbenes are extremely unstable due to their incomplete
electron octet and coordinative unsaturation, and they have only ever been thought
of as highly reactive transitory intermediates in organic transformations like cyclo-
propanation. Despite attempts at synthesis dating back to 1835 [1], it wasn’t until
groundbreaking investigations in the late 1980s and early 1990s that a free, uncoordi-
nated carbene was finally isolated and given a clear characterisation [2]. Bertrand and
colleagues described the creation of the first isolable carbene in a seminal study from
1988, stabilising it through advantageous interactions with nearby silicon and phos-
phorus substituents [3]. A nitrogen heterocycle with a carbene that can be isolated
and “bottled” was described by Arduengo et al. three years later [4]. The remarkable
stability and relatively easy synthesis of the first N-heterocyclic carbene (NHC),
1,3-di(adamantyl)imidazol-2-ylidene (IAd, compound labelled 1a), spurred an
explosion of experimental and theoretical studies, with libraries of novel NHCs being
synthesised and studied. These structural features were inspired by earlier insightful
studies by Wanzlick [5] and O fele [6] on metal-carbene complexes. As more of the
complex chemistry of these compounds has been uncovered and utilised as a result
of these discoveries, NHCs have been raised from simply laboratory curiosities to
substances of immense practical value. NHCs have several uses in some of the most

1
Electrophile and Lewis Acid

Figure 1.
Major applications of NHCs.

significant catalytic transformations in the chemical industry as good ligands for

transition metals, and their reactivity upon coordination to main group elements and
as organocatalysts has opened up new study avenues.
In order to serve as an introduction and reference for researchers interested in
investigating and using these significant chemicals, we have attempted to present
a condensed review of the features and wide range of uses of NHCs in this chapter.
Following a general overview of the structure and characteristics of NHCs, three
sections are loosely divided to discuss NHCs’ reactivity and uses in contemporary
chemistry. These sections cover their use as ligands for transition metals, when they
are coordinated to p-block elements, and as organocatalysts. For further in-depth
reading, each part includes a brief summary of the salient characteristics and essential
applications, as well as references to seminal works and thorough expert evaluations.
The discussion is highlighted by more thorough summaries of a few recent research
that illustrate the state of the art today and anticipated developments as an increasing
number of NHCs continue to find novel and interesting uses throughout the chemical
sciences (Figure 1).

2. Structure and general properties of NHCs

NHCs are categorised as heterocyclic entities with at least one nitrogen atom and a
carbene carbon inside the ring structure [7, 8]. Several diverse types of carbene com-
pounds with varying substitution patterns, ring diameters, and levels of heteroatom
stabilisation fit under these criteria [9]. The first known compound, IAd (1a), serves
as an illustration of the general structures of NHCs in Figure 2. The exceptional
stability of the carbene centre C2 can be partially explained by the overall electrical
and steric impact of these structural characteristics.
NHCs typically have bulky substituents next to the carbene carbon, as shown in
IAd by the two adamantyl groups attached to the nitrogen atoms. These substituents
work to kinetically stabilise the species by sterically disfavoring dimerization to the
corresponding olefin (the Wanzlick equilibrium). Yet, the nitrogen atoms’ ability to
stabilise electrons is a much more crucial feature. The highest occupied molecular
orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), which are
best defined as a formally sp2-hybridised lone pair and an unoccupied p-orbital at
the C2 carbon, respectively, in NHCs such as IAd are different from conventional
carbenes (Figure 3).
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Figure 2.
Structure of carbene.

Figure 3.
Molecular orbital diagram of NHC.

The nearby nitrogen atoms maintain this structure both mesomerically and induc-
tively by contributing electron density into the vacant p-orbital and reducing the
energy of the occupied s-orbital, respectively. Because NHCs are cyclic, this forces the
carbene carbon into a configuration that is more sp2-like and favours the singlet state.
The C-N bond lengths (1.37 A) found in IAd, which lie between those of its equivalent
imidazolium salt (IAdH1, 1.33 A)4 and its C2-saturated counterpart (IAdH2, 1.49
A) [10], reflect this ground-state structure and indicate that the C22 nitrogen bonds
have partial double-bond character. All classes of NHC can be stabilised using these
broad principles, however the proportional importance of each effect differs from
compound to compound (Figure 4).
Due to their partial aromaticity, NHCs generated from heteroaromatic compounds
benefit from a higher level of stability. As less proximal steric bulk is required due
to this effect, which has been estimated to be about 25 kcal/mol for model imidazol-
2-ylidenes [11], the simple methyl-substituted NHC 1,3- di(methyl)imidazol-2-ylidene
(IMe) is persistent in solution [12]. The first example of a stable carbene that does not
benefit from aromaticity was described by Arduengo and coworkers in 1995 [13] and
is known as 1,3-di(mesityl)imidazolin-2-ylidene (SIMes). Therefore, stabilising the
carbene centre does not need two nearby nitrogen atoms [14]. Stable carbenes con-
taining only one nitrogen substituent, as the series of cyclic (alkyl) (amino)carbenes
(CAACs,) discovered by Bertrand et al. [15], have also garnered significant research

Figure 4.
Different types of N-heterocyclic Carbenes.

3
Electrophile and Lewis Acid

interest. NHCs bearing alternate heteroatoms, such as sulphur and oxygen, are acces-
sible. When the carbene centre is generated at places other than C2, similar compounds
stabilised by a single nitrogen atom may arise. These mesoionic or “abnormal” car-
benes, for which it is impossible to sketch a neutral, non-zwitterionic carbene reso-
nance structure, tend to be more electron-donating than their “normal” equivalents
and can exhibit a wide range of distinct characteristics [16, 17]. There have also been
reports of remote NHCs, in which the carbene carbon is not located close to a nitrogen
heteroatom. The characteristics of the carbene can be significantly influenced by the
size and substitution pattern of the nitrogen heterocycle. Although while instances of
NHCs with smaller or bigger ring sizes, such as N, N9- diamidocarbenes (DACs), have
also been described, the greatest class of NHCs is still 5-membered rings. Due to the
higher N-C-N bond angle in these later compounds, which in turn effectively moves
the nitrogen substituents closer to the carbene centre, there is an increase in steric
shielding. Bigger rings also have an electrical impact because the cyclic structure’s
geometric constraints change the kind and extent of heteroatom stabilisation. It is
also important to note that numerous related groups of stable carbenes exist, which,
although not being NHCs, benefit from related methods of stabilisation. These include
cyclic derivatives and cyclic species featuring different ring heteroatoms such as
phosphorus instead of nitrogen [7, 14, 17].
Understanding the reactivity of NHCs is made possible by their ground-state
electrical structure. The lone pair located in the plane of the heterocyclic ring of
NHCs makes these compounds nucleophilic in contrast to the normal electrophilicity
of the majority of transitory carbenes. The main effect of this property is that NHCs
are inclined to function as s-donors and bind to a variety of metallic and non-metallic
species. The extraordinary power and distinctive characteristics of these interac-
tions, as well as their impact on the stability, structure, and reactivity of the resulting
complexes or adducts, are what have driven NHC interest to such a high level. The
following sections go into more detail about this extensive coordination chemistry
and the various applications of NHCs that result from it.
The relative simplicity with which libraries of structurally varied analogues may
be created and researched is another appealing aspect of NHCs. Synthetic approaches
to NHCs profit from years of study on the synthesis of heterocyclic compounds since,
in the majority of situations, the carbene is produced following deprotonation of the
matching cationic heterocyclic azolium salt [18]. The steric and electrical characteristics
of the resultant carbene may be easily changed for most classes of N-heterocycles by
simply changing the starting materials in a modular synthetic procedure. With various
kinds of heterocycles having essentially varied steric needs, the nitrogen-substituents or
other groups located next to C2 have the most impact on the steric environment at the
carbene centre. The heterocycle class is the main factor controlling the NHC electronics,
however the ring backbone substitution pattern is also crucial. The evaluation of these
characteristics enables straightforward comparisons between NHCs as well as between
NHCs and other related compounds like phosphines, enabling better informed choice
of the best carbene for any particular application [19, 20].

3. Coordination of NHCs to transition metals

The vast majority of N-heterocyclic carbene applications require coordination to

transition metals (Figure 5). About 20 years prior to the discovery of a free NHC,
Wanzlick [5] and Ofele [6] separately synthesised imidazol-2-ylidene-containing
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An Overview of N-Heterocyclic Carbene: Properties and Applications
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Figure 5.
Coordination of NHC to transition metals.

species carrying mercury(II) and chromium(0), respectively, in 1968. These reac-

tions resulted in the first instances of NHC-metal complexes. Before IAd was isolated,
Lappert and colleagues had carried out insightful experiments in the early 1970s
[21]. As was already indicated, NHCs aptitude as ligands for transition metals may
be explained by the fact that they naturally possess the capacity to donate an official
sp2-hybridised lone pair into an orbital of the transition metal.
Many groups have investigated the complete nature of bonding in these com-
plexes, and Cavallo and colleagues [22] and D’ez-Gonzalez and Nolan [23] have both
written reviews on the issue. While p-back-bonding into the carbene p-orbital and
p-donation from the carbene p-orbital may not have a significant impact, s-donation
is still the most significant factor in metal–ligand interaction. For instance, Frenking
and coworkers determined that group 11 metal-imidazol-2-ylidene and imidazolin-
2-ylidene complexes account for around 20% of the total bond energy [24]. In prac-
tice, metal-C-coordination is typically depicted as a single bond rather than a double
bond in actuality, with p-contributions limited to delocalization inside the NHC ring
(often depicted by a curved line between the ring heteroatoms). This illustration
highlights the distinctions between NHCs and traditional Fischer or Schrock carbene
ligands and most accurately captures the experimentally found potential for rotation
around the metal-C-bond. NHCs were previously thought of potential analogues
for this common class of auxiliary ligand in transition-metal coordination chemis-
try because of their strong s-donor and relatively weak p-acceptor features, which
resemble the coordination properties of phosphines [25].

4. Medicinal and materials applications of NHC-metal species

Organometallic materials can be developed because of the great thermal stability

of metal-NHC complexes and the possibility to customise their steric and electronic
properties [26]. In order to create organometallic complexes within the material’s
pores, imidazolium salts have been effectively coordinated to transition metals
when used as linker molecules in metal–organic frameworks [27]. It is also possible
for transition-metal complexes with hydrophobic long alkyl chain N-substituents
to self-assemble into extremely air- and moisture-resistant liquid crystals that are
thermally stable after the clearing point [28]. Many studies have been conducted
on the addition of NHC-metal complexes to the side chains or primary chain of
polymers. Bielawski and colleagues created a number of distinct palladium(II) and
5
Electrophile and Lewis Acid

Figure 6.
NHC showing medicinal properties.

platinum(II) organometallic polymers A using benzene-linked bis(NHC) units

which exhibit self-healing qualities due to the intrinsic reversibility of metal–ligand
coordination [29]. The conjugated bis-NHC linkers in these materials, which enable
electronic interaction between the two coordinated metal centers, make them promis-
ing as electrical conductors. There have also been reports of NHC-transition metal
complexes that function as phosphors and other photoactive substances [30]. The
therapeutic uses of NHC-transition-metal complexes as metallopharmaceuticals have
received more attention in recent years, with silver(I) and gold(I) species showing
particular promise as antibacterial and anticancer agents, respectively [31]. A variety
of Gram-positive and Gram-negative bacteria are resistant to several imidazol-2- and
imidazolin-2-ylidene-Ag complexes, which have astonishingly low minimum inhibi-
tory concentration values (10 mg/ ml21). These species often remain therapeutically
active for longer than the usual reference AgNO3, which might be explained by a
delayed release of active Ag1 ions from the NHC-stabilised complexes. Based on the
targeting of mitochondria, NHC -metal species containing gold have demonstrated
potential as anticancer medications. Since anticancer action is heavily dependent
on penetration across the mitochondrial membrane, it is essential for these systems
to be able to precisely control the lipophilicity of the complexes by change of the
N-substituents on the NHC. The cationic gold(I) complexes were demonstrated to
induce apoptosis by selective inhibition of the selenoenzyme thioredoxin reductase,
which is over expressed in many human cancers in a seminal publication by Berners-
Price, Filipovka and co-workers (Figure 6) [32].

5. NHCs as organocatalysts

A third significant class of applications, in which NHCs function as organocata-

lysts, has been made possible by their tendency to coordinate to carbon-electrophiles
[33, 34]. The bulk of these reactions begin as a result of a carbene’s nucleophilic
assault on carbonyl groups found in organic substrates. The majority of the trans-
formations that NHCs mediate as organocatalysts involve an initial assault of the
NHC onto a carbonyl group. The bulk of NHC-catalysed reactions use aldehydes as
substrates, in addition to trans esterification and related transformations of esters,
which are particularly relevant in the production of polymers. In these reactions,
the functional group is umpolunged, and the carbonyl carbon behaves more like a
transitory nucleophile than an electrophile. There are also other related transforma-
tions that include an umpolung at the b-position of α,β-unsaturated substrates. These
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Figure 7.
NHC as organocatalyst.

procedures involve direct NHC assault on α,β-unsaturated esters as well as “conjugate

umpolung” reactions of α,β-unsaturated aldehydes (Michael umpolung). Azolium
intermediates with leaving groups in the a-position or those produced from aldehydes
by in-situ oxidation constitute another family of reactions (Figure 7).
The cationic N-heterocyclic fragment created by nucleophilic attack is electron-
withdrawing by nature, which plays a crucial part in the adduct’s subsequent reactiv-
ity. An acyl azolium salt is produced in the case of esters by adding the NHC to the
carbonyl and then releasing the alkoxy group. This species may interact with alcohols
to produce transesterification products and is noticeably more electrophilic than the
parent ester. In step growth and ring-opening polymer synthesis, reactions of this
kind are often used, and NHCs provide an alternative to conventional organometal-
lic catalysts and initiators [35]. Due to their strong Bronsted basicity, NHCs play a
further role in these processes by hydrogen attaching to the alcohol and activating it
for nucleophilic attack.
The nucleophilic attack of NHCs on aldehydes leads to the widest and most
varied range of NHC-organocatalyzed reactions. The earliest instance of this type
of transformation, which was reported in 1943 by Ukai and colleagues and included
the homo-dimerization of aldehydes to benzoins catalysed by a thiazolium salt [36],
was not well understood at the time. The mechanism of this method is based on the
amphiphilic properties of an in situ produced NHC active catalyst, as suggested by
Breslow in 1958 [37]. The previously aldehydic proton in the resultant compound is
made acidic by the negative inductive impact of the cationic azolium group following
the first nucleophilic assault of the NHC on the aldehyde. The enamine-like “Breslow
intermediate”, which is nucleophilic at carbon as a result of p-donation from the ring
heteroatoms.
The isolation and characterisation of representative samples taken from SIPr by
Berkessel and coworkers [38] has recently validated the role of these species in NHC
organocatalysis. In the aforementioned benzoin condensation, product production is
caused by intermediate nucleophilic attack on another aldehyde equivalent followed
by the elimination of the NHC. The aldehyde substrate’s natural reactivity is effec-
tively flipped during the reaction (also known as “umpolung”), with the typically
electrophilic carbonyl carbon serving as a momentary nucleophile. Hence, umpolung
reactions of this kind are examples, and Breslow intermediates may be thought of as
acyl anion equivalents [39].
The study of NHC-catalysed umpolung has advanced significantly over the past
few decades, and [33, 34] Figure 8 provide an overview of the main reaction classes.
In general, pre-forming the free carbene is not necessary in reactions facilitated
by NHC coordinated with the transition-metal complexes. Rather, the equivalent
7
Electrophile and Lewis Acid

Figure 8.
Different reactivity of Breslow intermediate.

azolium salt precursor is often deprotonated in order to produce the active catalyst
in situ. The creation of asymmetric variants utilising chiral NHCs has significantly
increased the syntactic value of several of these transformations. The most successful
enantioselectivity-inducing catalysts have been those based on the triazol-2-ylidene
motif, with systems that include a chiral nitrogen substituent into a rigid polycyclic
structure being commonly used.
One geometric isomer of the Breslow intermediate is preferred over the other
when using these asymmetrical catalysts, and the electrophile approaches the least
hindered enantiotopic face. Since the benzoin condensation is reversible, the Breslow
intermediary may potentially attack other electrophiles nucleophilically. In particular,
aldehyde addition reactions to activated alkenes, like Michael acceptors, have received
a great deal of attention (the Stetter reaction). The researchers have been focusing
on expanding the pool of appropriate olefinic coupling partners for this process
[40]. Recently, the application of relatively electron-neutral styrene derivatives was
accomplished utilising an electron-rich 2,6-dimethoxyphenyl N-substituted triazol-
2-ylidene catalyst [41].
There are additional Breslow intermediate reactivity routes that do not need a
formal umpolung at the carbonyl carbon [42]. For instance, removing a leaving group
from the a-position can lead to the same kind of acyl azolium salts as those produced
by adding NHC to esters. Similar species can also be produced via the direct in situ
oxidation of the Breslow intermediate in the presence of an external oxidant or by
pre-oxidised substrates like ketenes. Upon addition-elimination of a nucleophile,
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An Overview of N-Heterocyclic Carbene: Properties and Applications
DOI: http://dx.doi.org/10.5772/intechopen.1001331

these intermediates may release the NHC fragment immediately, or they may first
react as enolate or enone equivalents with the azolium moiety as a bystander [43].
The reactivity of α,β-unsaturated aldehydes is a potent and well-studied class of
transformations. Because to the extended p-system of the Breslow-type intermedi-
ates produced with these substrates, nucleophilic attack may take place conjugately
to produce products with an umpolung at the β-position (referred to as a “conjugate
umpolung” [44]). In these methods, sterically demanding NHC catalysts that inhibit
competitive functionalization at the traditional “carbonyl” position are frequently
advantageous. The first conjugate addition of the NHC to the β-position as opposed
to the carbonyl group occurs in another category of reactions with a,b-unsaturated
carbonyl compounds. After this, the resultant adducts can react to produce products
that are a- or b-functionalized as a consequence of chemistry of the Morita-Baylis-
Hillman type or a formal umpolung at the b-position, respectively [45]. Accessing the
umpolung reactivity seen with aldehydes from other kinds of substrates is one very
fascinating topic of current study endeavour. Chi and coworkers recently published
an exquisite proof of this idea in a number of annulation reactions of saturated
aliphatic esters [46]. Figure 9 provides a mechanistic explanation for these events and
illustrates how the critical diamino dienol Breslow-type intermediate is formed. The
acyl azolium salt that results from the first nucleophilic addition-elimination of the
NHC to the ester group tautomerizes to produce an enol species. The azolium group
in this molecule has an electron-withdrawing property that makes the b-CH2 protons
very acidic. If there is an excess of DBU base (where DBU is 1,8-diazabicyclo [5.4.0]
undec-7-ene, 1.5–2 equiv.), deprotonation can take place to produce the homoenolate
equivalent. The high degree of conjugation present in the resultant intermediate with
b-aryl-substituted substrates can also help to explain the extraordinary selectivity
for this deprotonation step over more traditional a-functionalization methods. The
Breslow-type species, which may react as a nucleophile through conjugate umpol-
ung to produce b-functionalized products, is comparable to that synthesised under
standard circumstances using a,b-unsaturated aldehyde substrates.

Figure 9.
Mechanistic explanation for diamino dienol Breslow-type intermediate formation.

Figure 10.
Reaction of NHC with enones.

9
Electrophile and Lewis Acid

Aliphatic esters are often used as feedstocks in organic chemistry, but there are few
other synthetic techniques for specifically activating the b-position of these sub-
strates. This approach also permits high degrees of enantiocontrol during the annula-
tion processes utilising the chiral triazol-2-ylidene catalyst, delivering five-membered
heterocycles in enantiomeric ratios using enone, trifluoroketone, or hydrazone
electrophiles (the reaction with enones is shown in Figure 10).

6. Conclusions

One of the most significant achievements in contemporary chemical research

is undoubtedly the discovery and development of N-heterocyclic carbenes. Since
Arduengo and colleagues originally described the first “bottleable” NHC 23 years
ago, significant research on the structure, coordination chemistry, and reactivity
of these compounds by other groups has resulted in a wide range of applications
in numerous industries. NHCs are currently the mainstays of organic and organo-
metallic chemistry, competing with phosphines in the role of auxiliary ligands in
transition metal catalysis and opening up new avenues in main-group chemistry
and organocatalysis.
However, the rapid growth of NHCs is far from over, as our hope is evident from
the examples of current research discussed in this review. NHCs continue to play a
variety of novel functions in the chemical sciences in addition to their existing ones.
Heterogeneous catalysis is one promising area where the strength of NHC-metal
binding might provide improved stability of metallic colloids or surfaces with the
potential to change the catalyst’s capabilities by in situ functionalization of the ligand.
The growing usage of NHCs in metallopharmaceuticals may also be explained by the
stability and strength of the metal–ligand connection as well as the ease with which
one can modify the structural characteristics of organometallic complexes. The use of
NHCs is becoming more widely accepted in domains where significant progress is also
being achieved. Recent ground-breaking research in the field of organocatalysis has
concentrated on the creation of novel reactivity pathways that broaden the spectrum
of acceptable reaction partners beyond the conventional aldehydes.
The creation of novel NHCs with unique characteristics and reactivities is one
of the main forces behind the most innovative research currently being conducted.
In the area of homogeneous transition-metal catalysis, new chelating imidazolin-
2-ylidene ligands on ruthenium catalysts have made it easier to catalyse Z-selective
olefin metathesis, while recently created chiral NHC ligands have showed promise
in asymmetric hydrogenation processes. The stability of hitherto inaccessible non-
metallic species and the activation of tiny molecules have both been made possible by
new classes of NHCs, such as DACs and CAACs, which have displayed an unheard-of
reactivity. The recent report of an organic radical that had been stabilised by a CAAC
and was “bottleable” serves as an example of how well CAACs are suited to this type
of stabilisation. The future of NHCs appears to be highly promising given the signifi-
cant advancements made over the previous two decades and the high calibre research
now being carried out.

Acknowledgements

The authors are thankful to CSIR-IIIM Jammu to support this work.

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An Overview of N-Heterocyclic Carbene: Properties and Applications
DOI: http://dx.doi.org/10.5772/intechopen.1001331

Conflict of interest

The authors declare no conflict of interest.

Appendices and nomenclature

Ac Acetyl
aq Aqueous
Boc tert-Butoxycarbonyl
Bu n-Butyl
Bn Benzyl
CAN Ceric ammonium nitrate
CH3CN Acetonitrile
Cbz Benzyloxycarbonyl
CuAAC CuI-catalysed azide-alkyne cycloaddition
Cu(OAc)2 Copper acetate
CuSO4 Copper sulphate
Cy Cyclohexyl
d.r. Diastereomeric ratio
DCM Dichloromethane
DIAD Diisopropyl azodicarboxylate
DMF Dimethylformamide
DMSO Dimethylsulfoxide
Et Ethyl
h Hours
IPA Isopropanol
m.p. Melting point
Me Methyl
mCPBA Meta perchloro benzoic acid
min Minutes
n-Bu n-Butyl
NaN3 Sodium azide
NH3 Ammonia
NHC N-heterocyclic carbene
Ph Phenyl
Py Pyridine
Rf Retention factor
RT Room temperature
TBS tert-Butyldimethylsilyl
t
Bu tert-Butyl
TEA Triethylamine
Tf Trifluoromethanesulfonyl
TFA Trifluoroacetic acid
THF Tetrahydrofuran
Tosylate p-Toluenesulfonate
Triflate Trifluoromethanesulfonate
Ts p-Toluenesulfonyl

11
Electrophile and Lewis Acid

Author details

Norein Sakander1,2, Ajaz Ahmed1,2, Bisma Rasool1,2 and Debaraj Mukherjee1,2*

1 Academy of Scientific and Innovative Research, Ghaziabad, India

2 CSIR-Indian Institute of Integrative Medicine, Jammu, India

*Address all correspondence to: [email protected]

© 2023 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of
the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0),
which permits unrestricted use, distribution, and reproduction in any medium, provided
the original work is properly cited.
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An Overview of N-Heterocyclic Carbene: Properties and Applications
DOI: http://dx.doi.org/10.5772/intechopen.1001331

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