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ChemInform Abstract: A Palladium/Copper Bimetallic Catalytic System:

Dramatic Improvement for Suzuki-Miyaura-Type Direct C-H Arylation of
Azoles with Arylboronic Acids.

Article in Chemistry - A European Journal · October 2010

DOI: 10.1002/chem.201001338 · Source: PubMed

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DOI: 10.1002/chem.201001338

A Palladium/Copper Bimetallic Catalytic System: Dramatic Improvement for

Suzuki–Miyaura-Type Direct C H Arylation of Azoles with
ACHTUNGREArylboronic Acids

Bo Liu, Xurong Qin, Kaizhi Li, Xiyu Li, Qiang Guo, Jingbo Lan, and Jingsong You*[a]

The Suzuki–Miyaura coupling ranks as one of the most arylation of azoles with arylboronic acid hitherto. In this
powerful and reliable biaryl forming reactions.[1] Traditional- context, we wish to develop an efficient general methodolo-
ly, these transition-metal catalyzed cross-couplings require gy to achieve the direct Suzuki–Miyaura-type coupling of a
aryl halides or pseudohalides to react with boronic acids.[2] wide range of azoles with arylboronic acids.
As a variety of metal-mediated biaryl formations through Our initial exploration focused on the monometallic palla-
aromatic C H activation have been popularized, the dium(II)-catalyzed C H arylation of various azoles with ar-
Suzuki–Miyaura-type reactions, in which aryl halides or ylboronic acids in the presence of inorganic oxidants (e.g.,
pseudohalides are replaced by (hetero)arenes, have recently CuACHTUNGRE(OAc)2, Ag2CO3, and Ag2O), organic oxidants (e.g.,
attracted attention. This type of cross-coupling is not only DDQ (2,3-dichloro-5,6-dicyanobenzoquinone), and BQ
an efficient and complementary process to form biaryls, but (benzoquinone)), and/or dioxygen (O2). Whereas p-electron
also is in connection with sustainable chemistry. Whereas excessive five-membered heterocycles (i.e., thiophenes,
the Suzuki–Miyaura-type direct C H arylation of arenes furans, and pyrroles) smoothly coupled with arylboronic
(which generally require a directing group) has been devel- acids through an electrophilic mechanism, the azoles investi-
oped greatly,[3] the coupling of heteroarenes with arylboron- gated herein gave only trace amount to low yields of the de-
ic acids still remains elusive. In comparison with arenes, het- sired products.[4, 5] Although both types of heteroarenes are
eroarenes themselves are susceptible to oxidative homocou- electron-rich, the C2 sites of azoles are relatively electron-
pling and decomposition as well as self-coupling of arylbor- deficient. We believe that the distinctly differential p-elec-
onic acids in the presence of a PdII species. As far as we tronic characteristics may induce the clear distinctness of re-
know, only a few successful examples relative to heteroar- activity. Owing to the relatively acidic C2 sites, azoles are
enes have been described so far. Shi et al. described a PdII- unsusceptible to electrophilic C H substitution (SEAr) of
catalyzed cross-coupling of electron-rich heteroarenes (i.e., PdII under mild conditions. Considering that CuI salts have
pyrrole, furan, and thiophene derivatives) with arylboronic been used as catalysts or activators in direct C H arylations
acids under mild conditions.[4] Studer et al. reported the first of azoles,[7] we envisioned whether the additional introduc-
direct C H arylation of indoles with arylboronic acids and tion of a catalyic amount of CuI salt could assist the C2 H
the 2,2,6,6-tetramethylpiperidine N-oxyl radical (TEMPO) bond activation to generate an azole–copper species, which
as an external mild oxidant at room temperature.[5] Al- could undertake a transmetalation to arylpalladium(II) in-
though the aryl–azole structural motifs are ubiquitous in termediate to enable a catalytic cycle. Herein, we disclose
biologically important natural products, synthetic pharma- an efficient palladium/copper co-catalytic system for the
ceuticals, and materials,[6] it is unknown that the direct C H direct C H arylation of a variety of azoles with arylboronic
acids to extend current synthetic methodologies.
Xanthines (e.g., caffeine, theophylline, and theobromine)
[a] B. Liu, X. Qin, K. Li, X. Li, Q. Guo, Prof. Dr. J. Lan, Prof. Dr. J. You
Key Laboratory of Green Chemistry and are important biologically active alkaloids with imidazole
Technology of Ministry of Education skeletons. 8-(Hetero)aryl-substituted xanthines are highly
College of Chemistry, and State Key Laboratory of Biotherapy potent and selective antagonists at human A2B adenosine re-
West China Medical School, Sichuan University ceptors.[8] Following our continuing interest in the direct C
29 Wangjiang Road, Chengdu 610064 (P.R. China)
Fax: (+ 86) 28-85412203
arylation of xanthines, we initially focused on the heterocou-
E-mail: [email protected] pling of caffeine 1 with phenylboronic acid 2 a (Scheme 1).
Supporting information for this article is available on the WWW In this model reaction we screened several parameters (e.g.,
under http://dx.doi.org/10.1002/chem.201001338. oxidant, base, solvent, and additive) shown in Table 1.

11836  2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Chem. Eur. J. 2010, 16, 11836 – 11839
 COMMUNICATION
With optimized conditions now in hand, we explored the
scope of this methodology with respect to arylboronic acid
structure as summarized in Table 2. It was gratifying to find

Scheme 1. Direct C H arylation of caffeine with phenylboronic acid. Table 2. Catalytic C arylation of caffeine with various arylboronic acids.[a]

Table 1. Optimization of the coupling of caffeine with phenylboronic

acid.[a]
Entry Oxidant Base Additive Solvent Yield [%][b]
1 BQ KF – DMSO trace
2 DDQ KF – DMSO trace
3 O2 KF – DMSO trace
4 Ag2O KF – DMSO trace
5 Ag2CO3 KF – DMSO trace
6 CuACHTUNGRE(OAc)2 KF – DMSO 46
7 CuACHTUNGRE(OAc)2 K3PO4 – DMSO 42
8 CuACHTUNGRE(OAc)2 Cs2CO3 – DMSO 38
9 CuACHTUNGRE(OAc)2 Na2CO3 – DMSO 30
10 CuACHTUNGRE(OAc)2 TBAF·3H2O – DMSO trace
11 CuACHTUNGRE(OAc)2 KF – dioxane trace
12 CuACHTUNGRE(OAc)2 KF – o-xylene trace
13 CuACHTUNGRE(OAc)2 KF – DMF 56 [a] Conditions: Reactions were carried out by using PdACHTUNGRE(OAc)2 (5 mol %), Cu-
14 CuACHTUNGRE(OAc)2 KF – NMP 62
ACHTUNGRE(OAc)2 (1 equiv), KF (1 equiv), CuCl (10 mmol %), BQ (0.5 equiv), caffeine
15 CuACHTUNGRE(OAc)2 KF CuCl NMP 76 (0.5 mmol), and arylboronic acid (1.0 mmol) in a 0.5 m NMP solution for 30 h at
16 CuACHTUNGRE(OAc)2 KF CuBr NMP 66 80 8C (isolated yields in parentheses).
17 CuACHTUNGRE(OAc)2 KF CuCl + BQ NMP 82[c]
[a] Reactions were carried out by using PdACHTUNGRE(OAc)2 (5 mol %), CuACHTUNGRE(OAc)2
(1 equiv), base (1 equiv), copper(I) salt (10 mol %), caffeine (0.5 mmol),
that our catalyst system accelerated the arylation of caffeine
and phenylboronic acid (1 mmol) in a 0.5 m solution for 30 h at 80 8C.
[b] Isolated yields. [c] 0.5 equiv of BQ. DMSO = dimethyl sulfoxide, with a wide array of arylboronic acids. Whether the arylbor-
TBAF = tetra-n-butylammonium fluoride, DMF = N,N-dimethylforma- onic acids were electron-rich or electron-poor, all of them
mide, NMP = N-methyl-2-pyrrolidone. afforded good to excellent yields (Table 2, 3 a–k). Owing to
the importance of fluorobiaryl products in medicinal and
materials chemistry, fluoroarylboronic acids were investigat-
Among the oxidants investigated, CuACHTUNGRE(OAc)2 was the best ed accordingly. The reaction conditions were also suitable
choice (Table 1, entries 1–6). After screening a variety of for a variety of fluoroarylboronic acids (Table 2, 3 i–k).
bases (e.g., KF, K3PO4, Cs2CO3, Na2CO3, and TBAF·3H2O), We next applied this protocol to other xanthines to pre-
KF was found to be the most effective (Table 1, entries 6– pare 8-aryl theophylline and theobromine derivatives in
10). Subsequently, a 62 % yield of heterocoupling product good to excellent yields (Table 3, entries 4 a–c). Simple
was obtained in NMP by using one equivalent of KF as the purine heterocycles are attractive as “functional” p compo-
base and CuACHTUNGRE(OAc)2 as the oxidant (Table 1, entries 6 and nents in organic materials with biological relevance.[9] Re-
11–14). Excitingly, as a catalytic amount of CuI was em- cently, C arylation of purines has started to attract inter-
ployed as the co-catalyst, catalytic efficiency could be im- est.[10] Our methodology could be applicable to the synthesis
proved significantly. Copper(I) chloride was proven to be of various 8-arylated purines (Table 3, entries 4 d–f). In addi-
superior to other sources of the copper salt (Table 1, tion to these important alkaloids, this bimetallic catalytic
entry 15). system was proven to effectively promote the cross-coupling
It is well known that the transmetalation between arylbor- of a relatively wide range of azoles (e.g., benzoimidazole,
onic acids and PdII species readily leads to undesired homo- benzoxazole, thiazoles, and oxadiazoles) with arylboronic
coupling of arylboronic acids, which suppresses the genera- acids to give moderate to good yields with excellent regiose-
tion of the cross-coupling product. BQ has been widely used lectivity (at a relatively acidic CACHTUNGRE(sp2) position; Table 3, en-
as the oxidant or additive in some oxidative cross-coupling tries 4 g–m).
reactions. To our delight, addition of BQ restrained the ho- It is important to stress that the cross-coupling reactions
mocoupling to improve the yield of target compound upon of azoles investigated in Table 3 proceeded more sluggishly
to 82 % (Table 1, entry 17). Thus, the best result was ob- in the absence of CuCl, and the yields of aryl azoles general-
tained by using 1 equiv of CuACHTUNGRE(OAc)2 as the oxidant, 1 equiv ly decreased to around 15–30 %. Based on this observation,
of KF as the base, and 0.5 equiv of BQ as the additive in the this type of Suzuki–Miyaura coupling is assumed to mainly
presence of bimetallic catalytic system of PdACHTUNGRE(OAc)2 (5 involve two plausible catalytic routes: 1) The CuCl-mediated
mol %) and CuCl (10 mol %) in NMP at 80 8C for 30 h. process might occur through the formation of the azole–

Chem. Eur. J. 2010, 16, 11836 – 11839  2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.chemeurj.org 11837
 J. You et al.

Table 3. Catalytic C arylation of (hetero)arenes with boronic acids.[a] ylboronic acids (Scheme 3).[14] Interestingly, this bimetallic
catalytic method was capable of allowing the direct synthesis
of 3-arylated indolizines from indolizine through the C H
arylation with arylboronic acids in one step.

Scheme 3. Synthesis of 3-arylated indolizines.

In conclusion, we have developed for the first time a class

of Suzuki–Miyaura-type direct C H arylation of azoles in-
stead of azole halides or pseudohalides with arylboronic
acids. The bimetallic catalytic system not only allows the C
arylation of a broader spectrum of azoles with various aryl-
boronic acids under relatively mild conditions, but is also ap-
[a] Conditions: Reactions were carried out by using PdACHTUNGRE(OAc)2 (5 mol %), Cu- plied to the direct synthesis of 3-arylated indolizines from
ACHTUNGRE(OAc)2 (1 equiv), KF (1 equiv), CuCl (10 mmol %), BQ (0.5 equiv), hetero-
indolizines. We believe that this methodology would provide
ACHTUNGREarene (0.5 mmol), and arylboronic acid (1.0 mmol) in a 0.5 m NMP solution
for 30 h at 100 8C (isolated yields in parentheses). [b] 80 8C. [c] 120 8C. [d] Cu- a powerful complement for the traditional Suzuki–Miyaura
ACHTUNGRE(PPh3)2NO3 (10 mmol %) was added instead of CuCl. coupling reactions.

copper species IM2, and subsequent transmetalation with ar- Experimental Section
ylpalladium species IM1 to form the key heterocoupling in-
termediate IM3, followed by reductive elimination to pro- A flame-dried Schlenk test tube with a magnetic stirrer bar was charged
with PdACHTUNGRE(OAc)2 (5.6 mg, 0.025 mmol), N-heteroarene (0.5 mmol), arylbor-
duce the desired product. Pd0 could be reoxidized by Cu-
onic acid (1.0 mmol), CuACHTUNGRE(OAc)2 (0.5 mmol), CuCl (0.05 mmol), BQ
ACHTUNGRE(OAc)2 to complete the catalytic cycle; 2) Given that other (0.25 mmol), KF (0.5 mmol), and NMP (1.0 mL) under N2. A rubber
oxidants including inorganic oxidants, organic oxidants, and/ septum was replaced with a glass stopper, and the system was then evacu-
or dioxygen mentioned above were completely incapable of ated twice and back-filled with N2. The reaction mixture was stirred for
fulfilling the catalytic cycle, we rationalized that an (even 5 min at room temperature, and then heated at the indicated temperature
for 30 h. The reaction mixture was then cooled to ambient temperature,
catalytic) amount of copper(I) formed from CuACHTUNGRE(OAc)2 could
diluted with CH2Cl2 (20 mL), filtered through a celite pad, and washed
promote the formation of the azole–copper species to carry with CH2Cl2 (10–20 mL). The combined organic extracts were concen-
out the transmetalation in the absence of CuCl trated and the resulting residue was purified by column chromatography
(Scheme 2).[7, 11, 12] on silica gel to provide the desired product.

Acknowledgements
This work was supported by grants from the National NSF of China (Nos
20972102, 20872101 and 20772086) and PCSIRT (No IRT0846). We
thank the Centre of Testing & Analysis, Sichuan University for NMR
measurements.

Scheme 2. Plausible catalytic cycle of Suzuki–Miyaura-type direct C-aryl-

ACHTUNGREation of azoles with arylboronic acids. Keywords: bimetallic catalysis · C H activation · copper ·
heteroarenes · palladium · Suzuki–Miyaura coupling
Indolizine derivatives are a type of N-fused heterocycles
broadly found in biologically important natural products
and synthetic pharmaceuticals.[13] The synthesis of 3-arylated [1] a) D. S. Matteson, Stereodirected Synthesis with Organoboranes,
Springer, Berlin, 1995; b) N. Miyaura, Synthesis of Biaryls via the
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indolizine was first pre-activated to 3-chloroindolizine, and Organic Chemistry, Vol. 6 (Ed.: L. S. Liebeskind), JAI, Stamford,
then underwent a typical Suzuki–Miyaura coupling with ar- 1998, p. 187.

11838 www.chemeurj.org  2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Chem. Eur. J. 2010, 16, 11836 – 11839
 COMMUNICATION
Pd/Cu Bimetallic Catalytic System

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