FULL PAPER

DOI: 10.1002/ejoc.201001729

Homocoupling of Arylboronic Acids Catalyzed by CuCl in Air at Room

Temperature

Guanjun Cheng[a] and Meiming Luo*[a]

Keywords: Boron / Biaryls / Copper / C–C coupling / Homogeneous catalysis

Homocoupling of arylboronic acids has been successfully loading of 2 mol-% under extremely mild conditions: in air,
carried out by using the inexpensive simple copper salt CuCl at room temperature, without the need of any additives such
as the catalyst in methanol to obtain symmetric biaryls in as base, oxidant, or ligand.
good to excellent yields. The reaction proceeds with a CuCl

aryls.[6a,6c–6g,7b–7e,8a,8c–8f,9,11] (4) Some reactions even require

Introduction
heating.[6b,6c,6e,7a,8b,8c,9b,10c] Other metals such as Au,[12]
Rh,[13] Ni,[14] Cr,[15] and Cu[16–18] have recently been used to
Biaryls synthesized by C–C bond-forming reactions are
promote the homocoupling of arylboronic acids. Au and
important building blocks for functional materials and nat-
Rh are expensive and some additives are necessary for catal-
ural products.[1] Developing straightforward and environ-
ysis.[12,13] The Ni catalytic system employed malodorous
mentally friendly reactions for the preparation of biaryls
pyridine as the solvent and required heating.[14] In the chro-
continues to be the subject of intense investigation. Great
mium-mediated homocoupling of arylboronic acids, Ag2O
progress in the synthesis of symmetrical and unsymmetrical
(3 equiv.) is required as an expensive oxidant to restore the
biaryls has been achieved by transition-metal-catalyzed
catalyst, and the reaction was performed with heating.[15]
couplings such as the Suzuki reaction,[2] modified Ullmann
Three papers report that certain copper species can be used
reaction,[3] Kumada–Corriu–Tamao reaction,[4] and so on.
to mediate the homocoupling of arylboronic acids. Demir
For the synthesis of symmetrical biaryls, the Ullmann cou-
and co-workers have shown that homocoupling of aryl-
pling reaction, which has been known for a century, has
boronic acids can be carried out in DMF in the presence
gained much attention as an efficient process.[5] On the
of Cu(OAc)2 without any additive such as a base or a li-
other hand, oxidative dimerization of organometallic spe-
gand.[16] However, this reaction requires a substoichi-
cies has emerged as another choice. Because arylboronic ac-
ometric amount of Cu(OAc)2 (0.5 equiv.) and a relatively
ids prepared from the corresponding aryl halides are more
high reaction temperature (100 °C). When the amount of
stable and less toxic than many other organometallic rea-
Cu(OAc)2 was decreased to 10 mol-% in several examples,
gents, it is not surprising that many studies have been re-
an oxygen atmosphere and 4-Å molecular sieves were re-
ported recently on the oxidative homocoupling of aryl-
quired. Yamamoto and co-workers reported that the homo-
boronic acids as an excellent method to obtain symmetrical
coupling reaction of arylboronic acids was catalyzed by a
biaryls. Palladium-based catalysts are most frequently used
copper complex employing 1,10-phenanthroline as li-
for the homocoupling of arylboronic acids.[6–11] However,
gand.[17] During the preparation of this manuscript, Kabou-
there are limitations and room for improvement in these
din and co-workers reported that inexpensive copper(II)
catalytic methods exists: (1) Palladium is expensive and ad-
sulfate could mediate the homocoupling of arylboronic ac-
ditional ligands are usually required.[6,10a,11] (2) Certain oxi-
ids. This method requires a stoichiometric amount of
dants are employed to restore the catalyst.[8b–8g,9a] (3) Ad-
CuSO4 and heating in uneasily handled DMF.[18] In ad-
dition of a base is necessary to acquire high yields of bi-
dition to metal-mediated homocoupling, Shi and co-
workers reported the iodine-promoted homocoupling of ar-
ylboronic acids in PEG-400 under aerobic conditions.[19]
[a] Key Laboratory of Green Chemistry & Technology of Ministry This reaction required a relatively high temperature (100–
of Education at Sichuan University, College of Chemistry, 140 °C) and long reaction time (48 h). In this paper, we re-
Sichuan University,
Chengdu 610064, People’s Republic of China port an easy and efficient copper-catalyzed homocoupling
Fax: +86-28-85462021 reaction of arylboronic acids for the synthesis of symmetri-
E-mail: luomm@scu.edu.cn
Supporting information for this article is available on the cal biaryls under mild conditions without the need of any
WWW under http://dx.doi.org/10.1002/ejoc.201001729. additives.

Eur. J. Org. Chem. 2011, 2519–2523 © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2519
 G. Cheng, M. Luo
FULL PAPER
Results and Discussion Table 1. Copper-catalyzed homocoupling of arylboronic acid: opti-
mization of the reaction conditions.[a]
Initially, the symmetric biaryl byproducts encountered in
some Cu-catalyzed C–N bond-forming reactions of aryl-
boronic acids[20–22] attracted our attention. We surmised
that certain simple copper salts may be used as efficient
catalysts for the homocoupling of arylboronic acids under
mild conditions. During optimization studies, 3-nitrophen-
ylboronic acid was chosen as the model substrate, and all Entry Catalyst Solvent Base Time Yield
(mol-%) [h] [%][b]
the reactions were conducted at room temperature in air.
Solvents, catalysts, and bases were investigated. As shown 1 Cu (2) MeOH – 15 73
2 Cu2O (2) MeOH – 20 57
in Table 1, various copper salts (2 mol-%) were tested with-
3 CuI (2) MeOH – 20 55
out any additives such as base, oxidant, or ligand (Table 1, 4 CuCl (2) MeOH – 4 93
Entries 1–6). The best activity was shown with CuCl, which 5 CuCl2 (2) MeOH – 15 86
gave not only the best yield, but also the shortest reaction 6 Cu(OAc)2 (2) MeOH – 15 77
time (Table 1, Entry 4). Other copper salts were less active 7 CuCl (10) MeOH – 2 86
8 CuCl (5) MeOH – 2.5 89
than CuCl, though they could afford symmetric biaryls. 9 CuCl (3) MeOH – 3 91
The influence of the amount of CuCl on the catalytic reac- 10 CuCl (1) MeOH – 15 78
tions was also investigated (Table 1, Entries 4 and 7–11). 11 – (0) MeOH – 20 0
The results show that a CuCl loading of 2 mol-% gave the 12 CuCl (2) EtOH – 24 59
13 CuCl (2) H2O – 24 57
best homocoupling product yield (Table 1, Entry 4). The
14 CuCl (2) iPrOH – 24 15
homocoupling reaction did not occur in the absence of a 15 CuCl (2) THF – 24 8
copper catalyst (Table 1, Entry 11). We next examined the 16 CuCl (2) DMF – 24 67
effect of the solvent (Table 1, Entries 4 and 12–19), and 17 CuCl (2) acetone – 24 trace
methanol was found to be the best of choice (Table 1, En- 18 CuCl (2) MeOH/H2O (1:1)[c] – 16 78
19 CuCl (2) EtOH/H2O (1:1)[c] – 16 48
try 4). It is well known that the addition of a base can im- 20 CuCl (2) MeOH NEt3 4 82
prove the reaction efficiency for some catalytic sys- 21 CuCl (2) MeOH Na2CO3 20 14
tem.[6a,6c–6g,7b–7e,8a,8c–8f,9,11] Subsequently, the reaction was 22 CuCl (2) MeOH K2CO3 20 4
investigated in the presence of different bases (Table 1, En- 23[d] CuCl (2) MeOH – 3 90
tries 20–22). Interestingly, it was found that some inorganic [a] Reaction conditions: 3-nitrophenylboronic acid (0.75 mmol),
bases, such as Na2CO3 and K2CO3, inhibited rather than solvent (2.0 mL), room temperature, air. [b] Yield of isolated prod-
promoted the homocoupling reaction, giving very poor uct. [c] v/v. [d] Air was bubbled through the reaction mixture.
yields (Table 1, Entries 21 and 22). On the other hand, NEt3
as an organic base had little effect on the reaction (Table 1,
Entry 20). It was not necessary to bubble air through the catalytic system, it is noteworthy that the reaction of p-bro-
reaction mixture, though it could shorten the reaction time mophenyl boronic acid (1m) furnished the desired product
(Table 1, Entries 4 and 23). Thus, the optimized reaction 4,4⬘-dibromobiphenyl (2m) in 74 % isolated yield (Table 2,
conditions for the homocoupling of arylboronic acids in- Entry 13), demonstrating good selectivity. Careful inspec-
volve the use of CuCl (2 mol-%) as the catalyst, methanol tion of the results revealed that para- and meta-substituted
as the solvent, in air, at ambient temperature, and without arylboronic acids gave biaryls in good to excellent yields.
any additives such as base, oxidant, or ligand. Diverse results were obtained for ortho-substituted aryl-
Having defined the optimized reaction conditions, we in- boronic acids. o-Tolylboronic acid (1n) produced the corre-
vestigated the scope of the CuCl-catalyzed homocoupling sponding product 2,2⬘-dimethylbiphenyl (2n) in a lower
reaction with respect to the boronic acids. As shown in yield of 43 % (Table 2, Entry 14). With anthracene-9-yl-
Table 2, most of the substrates with a variety of substituents boronic acid (1o), only a trace amount of self-coupling
afforded the products in good to excellent yields under the product 2o was formed and the major product was the pro-
optimum reaction conditions. Phenylboronic acids bearing todeboronation product anthracene (Table 2, Entry 15). Re-
electron-withdrawing nitro, cyano, fluoro, trifluoromethyl, action with 2-naphthylboronic acid (1p) afforded corre-
and methoxycarbonyl groups gave corresponding homo- sponding dimer 2p in 90 % yield (Table 2, Entry 16), and
coupling products 2a–f in good yields (73–93 %; Table 2, phenanthren-9-ylboronic acid (1q) gave 9,9⬘-biphen-
Entries 1–6). We next examined the homocoupling reaction anthrene (2q) in 83 % yield (Table 2, Entry 17). The proto-
of aromatic boronic acids bearing electron-donating groups. col was also applied to the homocoupling of styrylboronic
Phenylboronic acids bearing methyl, tert-butyl, methoxy, acid (1r), giving desired product 2r in 77 % yield (Table 2,
dimethoxy, and propylsulfanyl (strongly coordinating)[17] Entry 18). Finally, the homocoupling of heteroarylboronic
groups gave desired product 2g–k in 73–92 % yields acids 2-thienylboronic acid (1s) and 3-pypridylboronic acids
(Table 2, Entries 7–11). It has been reported that some cop- (1t) gave corresponding products 2s and 2t in 21 and 63 %
per species can mediate the Suzuki–Miyaura cross-coupling yield, respectively, under the same reaction conditions
of arylboronic acids with arylbromides.[23] With the present (Table 2, Entries 19 and 20).

2520 www.eurjoc.org © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Eur. J. Org. Chem. 2011, 2519–2523
Homocoupling of Arylboronic Acids Catalyzed by CuCl

Table 2. Copper-catalyzed homocoupling of various arylboronic acids.[a]

[a] Reaction conditions: 1 (0.75 mmol), CuCl (0.015 mmol, 1.5 mg), MeOH (2.0 mL), room temperature (ca. 25 °C), air. [b] Isolated yield.
[c] Major product was anthracene. [d] MeOH (5.0 mL).

The coupling between two different arylboronic acids
was also tested under the optimum reaction conditions. As
shown in Scheme 1, the cross-experiments were performed
by combining two arylboronic acids with different and sim-
ilar electron density. In addition to the homocoupling prod-
ucts of the individual arylboronic acid components, GC–
MS analysis showed that the unsymmetrical biaryls from
the cross-coupling of two different arylboronic acids were
also formed. No significant selectivity was observed.
Demir,[16] Yamamoto,[17] and Kaboudin[18] inspected the
Cu-mediated homocoupling of arylboronic acids and pro-
posed putative mechanisms for the transformation. How-
ever, the mechanism of the copper-catalyzed homocoupling
reaction is not yet obvious at the present stage. The follow-
ing observations may be useful to speculate on the mecha-
nism: (1) Copper of any oxidation state, Cu0, CuI, or CuII,
is catalytically active in the homocoupling (Table 1). (2) Air
is critical to the reaction. (3) The negative counterion plays
an important role, and Cl– is the best for CuI catalysts
(Table 1). (4) Solvent affects the catalyst activity signifi-
cantly. On the basis of these observations and the proposed
mechanisms in the literature,[16–18] possible catalytic cycles
for Cu0, CuI, and CuII are depicted in Scheme 1. It seems
that there are three possible reaction pathways. The first
one is the CuI/CuIII catalytic cycle. Transmetalation of aryl-
boronic acid with CuI produces CuI–Ar, which reacts with
another arylboronic acid in the presence of oxygen to gen-
erate Ar–CuIII–Ar; this species releases CuI by reductive eli-
mination of homocoupling product Ar–Ar. The second one
is the Cu0/CuII cycle. Double transmetalation of CuII with
two molecules of arylboronic acid affords Ar–CuII–Ar,
which releases Cu0 by reductive elimination of product Ar–
Ar. Air oxidation of Cu0 reproduces CuII. The third pos-
sibility is the Cu0/CuI/CuII cycle, in which the Ar–CuII–Ar
intermediate may be produced either by double transmet-
alation of CuII with two molecules of arylboronic acid or
by disproportion of Ar–CuI. In view of the fact that CuICl
is more effective than CuIICl2 under the same reaction con-

Eur. J. Org. Chem. 2011, 2519–2523 © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.eurjoc.org 2521

FULL PAPER
Scheme 1. Coupling of different arylboronic acids.
ditions (Table 1, Entries 4 and 5), the homocoupling of ar-
ylboronic acids may take place most probably through the
CuI/CuIII catalytic cycle (Scheme 2). Considering that there
is no information currently available on the active species,
it is hard to tell the real reaction pathway.
Scheme 2. Plausible mechanism for the homocoupling of aryl-
boronic acids catalyzed by copper species.
Conclusions
In conclusion, we have successfully developed a simple
and efficient copper-catalyzed method for the homocou-
pling of arylboronic acids for the synthesis of symmetrical
2522 www.eurjoc.org © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
G. Cheng, M. Luo
biaryls. This method allows the use of the readily available,
inexpensive copper salt CuCl as the catalyst and offers very
good results for most arylboronic acids. The homocoupling
reaction proceeds in economical and easily handled meth-
anol under extremely mild conditions: in air, at room tem-
perature, and without any additives such as base, oxidant,
or ligand. With these novel features, the present simple cop-
per salt based catalytic system is much superior to the
known protocols documented in the literature. That some
inorganic bases such as Na2CO3 and K2CO3 can inhibit the
homocoupling reaction of arylboronic acids, which is often
encountered as a serious side reaction in some arylboronic
acid involved reactions, is an interesting finding. The good
selectivity of homocoupling over the Suzuki cross-coupling
shows potential application in synthesis and merits further
investigation.
Experimental Section
General Remarks: All reagents were purchased from commercial
suppliers and used without further purification. Both copper(I)
chlorides of 97.0+% and 99.999 % purity were tested and showed
almost the same reactivity. CuCl (97.0+%) was also examined by
ICP-MS, and no palladium was detected. Column chromatography
was performed with silica gel (200–300 mesh). Thin layer
chromatography was carried out by using Merck silica gel GF254
plates. 1H NMR (400 MHz) and 13C NMR (100 MHz) spectra
were recorded in CDCl3. Chemical shifts are reported in ppm using
TMS as internal standard. Splitting patterns are designated as fol-
lows: s, singlet; d, doublet; t, triplet; m, multiplet. Products were
characterized by comparison of 1H and 13C NMR spectroscopic
data with those in the literatures.
Representative Procedure for the CuCl-Catalyzed Homocoupling of
Arylboronic Acid 1a To Afford Biaryl 2a: A solution of CuCl
(1.5 mg, 0.015 mmol) and 3-nitrophenylboronic acid (125 mg,
0.75 mmol) in MeOH (2 mL) was stirred at 25 °C for 4 h in air.
The reaction mixture was filtered and washed with ethyl acetate.
The combined filtrate was concentrated in vacuo. The residue was
purified by flash chromatography on silica gel column (ethyl acet-
ate/petroleum ether, 1:5) to afford 2a (85.0 mg, 93 %) as a light
yellow solid.
Representative Procedure for the CuCl-Catalyzed Coupling of 1a and
1g To Afford Biaryls 2a, 3a, and 2g: A solution of 3-nitrophenylbo-
ronic acid (50 mg, 0.3 mmol), 4-methoxyphenylboronic acid
(45.6 mg, 0.3 mmol), and CuCl (1.1 mg, 0.012 mmol) in MeOH
(1.5 mL) was stirred at 25 °C for 4 h in air. The reaction mixture
was filtered and washed with ethyl acetate. The combined filtrate
was analyzed by GC–MS.
Supporting Information (see footnote on the first page of this arti-
cle): Characterization data and copies of the 1H and 13C NMR
spectra of the coupling products.
Acknowledgments
This work was supported by the National Natural Science Founda-
tion of China (21021001, 21072134) and Program for Changjiang
Scholars and Innovative Research Team in University (IRT0846).
We thank the Analytical & Testing Centre of Sichuan University
for NMR measurements.
Eur. J. Org. Chem. 2011, 2519–2523
Homocoupling of Arylboronic Acids Catalyzed by CuCl
[1] a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457–2483; b)
D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev. 2003,
103, 893–930; c) P. Lloyd-Williams, E. Giralt, Chem. Soc. Rev.
2001, 30, 145–157; d) H. Meier, Angew. Chem. Int. Ed. 2005,
44, 2482–2506.
[2] a) N. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott,
S. P. Nolan, J. Am. Chem. Soc. 2006, 128, 4101–4111; b) G. P.
McGlacken, L. M. Bateman, Chem. Soc. Rev. 2009, 38, 2447–
2464.
[3] J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire,
Chem. Rev. 2002, 102, 1359–1469.
[4] a) L. Monnereau, D. Sémeril, D. Matt, L. Toupet, A. J. Motac,
Adv. Synth. Catal. 2009, 351, 1383–1389; b) J. P. Corbet, G.
Mignani, Chem. Rev. 2006, 106, 2651–2710.
[5] A. Monopoli, V. Calò, F. Ciminale, P. Cotugno, C. Angelici,
N. Cioffi, A. Nacci, J. Org. Chem. 2010, 75, 3908–3911.
[6] a) Z. Jin, S. X. Guo, X. P. Gu, L. L. Qiu, H. B. Song, J. X.
Fang, Adv. Synth. Catal. 2009, 351, 1575–1585; b) L. Zhou,
Q. X. Xu, H. F. Jiang, Chin. Chem. Lett. 2007, 18, 1043–1046;
c) J. S. Yadav, K. U. Gayathri, H. Ather, H. Rehman, A. R.
Prasad, J. Mol. Catal. A 2007, 271, 25–27; d) M. J. Burns,
I. J. S. Fairlamb, A. R. Kapdi, P. Sehnal, R. J. K. Taylor, Org.
Lett. 2007, 9, 5397–5400; e) M. S. Wong, X. L. Zhang, Tetrahe-
dron Lett. 2001, 42, 4087–4089; f) D. J. Koza, E. Carita, Syn-
thesis 2002, 2183–2186; g) B. Mu, T. Li, Z. Fu, Y. Wu, Catal.
Commun. 2009, 10, 1497–1501; h) S. Punna, D. D. Diaz, M. G.
Finn, Synlett 2004, 2351–2354.
[7] a) J. S. Chen, K. Krogh-Jespersen, J. G. Khinast, J. Mol. Catal.
A 2008, 285, 14–19; b) G. Cravotto, M. Beggiato, A. Penoni,
G. Palmisano, S. Tollari, J. M. Lévěquec, W. Bonrathd, Tetra-
hedron Lett. 2005, 46, 2267–2271; c) N. Wu, X. Li, X. Xu, Y.
Wang, Y. Xu, X. Chen, Lett. Org. Chem. 2010, 7, 11–14; d) G.
Cravotto, G. Palmisano, S. Tollari, G. M. Nano, A. Penoni,
Ultrason. Sonochem. 2005, 12, 91–94; e) K. A. Smith, E. M.
Campi, W. R. Jackson, S. Marcuccio, C. G. M. Naeslund, G. B.
Deacon, Synlett 1997, 131–132.
[8] a) Z. Xu, J. Mao, Y. Zhang, Catal. Commun. 2008, 9, 97–100;
b) C. Amatore, C. Cammoun, A. Jutand, Eur. J. Org. Chem.
2008, 4567–4570; c) K. Cheng, B. Xin, Y. Zhang, J. Mol. Catal.
A 2007, 273, 240–243; d) K. Mitsudo, T. Shiraga, D. Kagen,
D. Shi, J. Y. Becker, H. Tanaka, Tetrahedron 2009, 65, 8384–
8388; e) G. W. Kabalka, L. Wang, Tetrahedron Lett. 2002, 43,
3067–3068; f) J. P. Parrish, Y. C. Jung, R. J. Floyd, K. W. Jung,
Eur. J. Org. Chem. 2011, 2519–2523 © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Tetrahedron Lett. 2002, 43, 7899–7902; g) L. M. Klingensmith,
N. E. Leadbeater, Tetrahedron Lett. 2003, 44, 765–768.
[9] a) K. Mitsudo, T. Shiraga, H. Tanaka, Tetrahedron Lett. 2008,
49, 6593–6595; b) A. Prastaro, P. Ceci, E. Chiancone, A. Boffi,
G. Fabrizi, S. Cacchi, Tetrahedron Lett. 2010, 51, 2550–2552.
[10] a) Y. Yamamoto, Synlett 2007, 1913–1916; b) Y. Yamamoto,
R. Suzuki, K. Hattori, H. Nishiyama, Synlett 2006, 1027–1030;
c) C. Zhou, R. C. Larock, J. Org. Chem. 2006, 71, 3184–3191.
[11] a) A. Ciric, F. Mathey, Organometallics 2010, 29, 4785–4786;
b) M. Wakioka, M. Nagao, F. Ozawa, Organometallics 2008,
27, 602–608.
[12] a) H. Tsunoyama, H. Sakurai, N. Ichikuni, Y. Negishi, T. Tsu-
kuda, Langmuir 2004, 20, 11293–11296; b) C. González-Arel-
lano, A. Corma, M. Iglesias, F. Sánchez, Chem. Commun. 2005,
1990–1992; c) N. G. Willis, J. Guzman, Appl. Catal. A: Gen.
2008, 339, 68–75; d) S. Carrettin, J. Guzman, A. Corma, An-
gew. Chem. Int. Ed. 2005, 44, 2242–2245.
[13] T. Volgler, A. Studer, Adv. Synth. Catal. 2008, 350, 1963–1967.
[14] G. Y. Liu, Q. L. Du, J. J. Xie, K. L. Zhang, X. C. Tao, Chin. J.
Catal. 2006, 27, 1051–1052.
[15] J. R. Falck, S. Mohapatra, M. Bondlela, S. K. Venkataraman,
Tetrahedron Lett. 2002, 43, 8149–8151.
[16] A. S. Demir, ö. Reis, M. Emrullahoglu, J. Org. Chem. 2003, 68,
10130–10134.
[17] N. Kirai, Y. Yamamoto, Eur. J. Org. Chem. 2009, 1864–1867.
[18] B. Kaboudin, T. Haruki, T. Yokomatsu, Synthesis 2011, 91–95.
[19] J. Mao, Q. Hua, G. Xie, Z. Yao, D. Shi, Eur. J. Org. Chem.
2009, 2262–2266.
[20] C. He, C. Chen, J. Cheng, C. Liu, W. Liu, Q. Li, A. Lei, Angew.
Chem. Int. Ed. 2008, 47, 6414–6417.
[21] a) D. M. T. Chan, K. L. Monaco, R. P. Wang, M. P. Winters,
Tetrahedron Lett. 1998, 39, 2933–2936; b) H. Rao, H. Fu, Y.
Jiang, Y. Zhao, Angew. Chem. Int. Ed. 2009, 48, 1114–1116; c)
J. P. Collman, M. Zhong, C. Zhang, S. Costanzo, J. Org. Chem.
2001, 66, 7892–7897; d) E. R. Strieter, B. Bhayana, S. L. Buch-
wald, J. Am. Chem. Soc. 2009, 131, 78–88.
[22] N. Xia, M. Taillefer, Angew. Chem. Int. Ed. 2009, 48, 337–339.
[23] a) J. Mao, J. Guo, F. Fang, S. J. Ji, Tetrahedron 2008, 64, 3905–
3911; b) Y. M. Ye, B. B. Wang, D. Ma, L. X. Shao, J. M. Lu,
Catal. Lett. 2010, 139, 141–144; c) M. B. Thathagar, J. Beckers,
G. Rothenberg, J. Am. Chem. Soc. 2002, 124, 11858–11859; d)
J. H. Li, J. L. Li, D. P. Wang, S. F. Pi, Y. X. Xie, M. B. Zhang,
X. C. Hu, J. Org. Chem. 2007, 72, 2053–2057.
Received: December 27, 2010
Published Online: March 14, 2011
www.eurjoc.org 2523