CuSO4-Mediated Homocoupling
of Arylboronic Acids under Ligand- and Base-Free Conditions in Air

Babak Kaboudin; Terumitsu Haruki; Tsutomu Yokomatsu

doi:10.1055/s-0030-1258321

PAPER

CuSO₄-Mediated Homocoupling of Arylboronic Acids under Ligand- and Base-Free Conditions in Air

Babak Kaboudin*^a,b, Terumitsu Haruki^b, Tsutomu Yokomatsu*^b
^a Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan 45137-66731, Iran
Fax: +98(241)4214949; e-Mail: kaboudin@iasbs.ac.ir;
^b School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horonouchi, Hachioji, Tokyo 192-0392, Japan
Fax: +81(42)676 3239; e-Mail: yokomatu@ps.toyaku.ac.jp;

Abstract

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Abstract

The homocoupling of arylboronic acids mediated by very inexpensive and air stable copper(II) sulfate in N,N-dimethylformamide affords the corresponding symmetrical biaryls in moderate to good yields. The homocoupling reaction proceeds in air at 50 ˚C in the presence of molecular sieves without any additives such as base and ligand.

Key words

homocoupling - arylboronic acids - copper(II) sulfate - biaryls

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References

<A NAME="RZ24210SS-1A">1a</A> Croom KF. Keating GM. Cardiovasc AJ. Drugs 2004, 64: 395

<A NAME="RZ24210SS-1B">1b</A> Sharpe M. Jarvis B. Goa KL. Drugs 2001, 61: 1501

<A NAME="RZ24210SS-1C">1c</A> Bemis GW. Murcko MA. J. Med. Chem. 1996, 39: 2887

<A NAME="RZ24210SS-1D">1d</A> Hajduk PJ. Bures M. Praestgaard J. Fesik EW. J. Med. Chem. 2000, 43: 3443

<A NAME="RZ24210SS-1E">1e</A> Bringmann G. Menche D. Acc. Chem. Res. 2001, 34: 615

<A NAME="RZ24210SS-2A">2a</A> Bringmann G. Günther C. Ochse M. Schupp O. Tasler S. Biaryls in Nature: A Multi-Faceted Class of Stereochemically, Biosynthetically, and Pharmacologically Intriguing Secondary Metabolites Springer; New York: 2001.

<A NAME="RZ24210SS-2B">2b</A> Horton DA. Bourne GT. Smythe ML. Chem. Rev. 2003, 103: 893

<A NAME="RZ24210SS-2C">2c</A> Lloyd-Williams P. Giralt E. Chem. Soc. Rev. 2001, 30: 145

<A NAME="RZ24210SS-2D">2d</A> Meier H. Angew. Chem. Int. Ed. 2005, 44: 2482

<A NAME="RZ24210SS-3A">3a</A> Suzuki A. Cross-Coupling Reaction of Organoboron Compounds with Organic Halides, In Metal-Catalysed Cross-Coupling Reactions Diederich F. Stang PT. Wiley-VCH; Weinheim: 1998.

<A NAME="RZ24210SS-3B">3b</A> Stanforth SP. Tetrahedron 1998, 54: 263

<A NAME="RZ24210SS-4A">4a</A> Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

<A NAME="RZ24210SS-4B">4b</A> Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

<A NAME="RZ24210SS-4C">4c</A> Suzuki A.
J. Organomet. Chem. 1999, 576: 147

<A NAME="RZ24210SS-5A">5a</A> Kirai N. Yamamoto Y. Eur. J. Org. Chem. 2009, 1864

<A NAME="RZ24210SS-5B">5b</A> Mao J. Hua Q. Xie G. Yao Z. Shi D. Eur. J. Org. Chem. 2009, 2262

<A NAME="RZ24210SS-5C">5c</A> Yoshida H. Yamaryo Y. Ohshita J. Kunai A. Tetrahedron Lett. 2003, 44: 1541

<A NAME="RZ24210SS-5D">5d</A> Wong MS. Zhang XL. Tetrahedron Lett. 2001, 42: 4087

<A NAME="RZ24210SS-5E">5e</A> Lei A. Zhang X. Tetrahedron Lett. 2002, 43: 2525

<A NAME="RZ24210SS-6A">6a</A> Miyaura N. Suzuki A. Main Group Met. Chem. 1987, 10: 295

<A NAME="RZ24210SS-6B">6b</A> Koza DJ. Carita E. Synthesis 2002, 2183

<A NAME="RZ24210SS-6C">6c</A> Kabalka GW. Wang L. Tetrahedron Lett. 2002, 43: 3067

<A NAME="RZ24210SS-6D">6d</A> Parrish JP. Jung YC. Floyd RJ. Jung KW. Tetrahedron Lett. 2002, 43: 7899

<A NAME="RZ24210SS-6E">6e</A> Klingensmith LM. Leadbeater NE. Tetrahedron Lett. 2003, 44: 765

<A NAME="RZ24210SS-6F">6f</A> Yamamoto Y. Suzuki R. Hattori K. Nishiyama N. Synlett 2006, 1027

<A NAME="RZ24210SS-7A">7a</A> Amatore C. Cammoun C. Jutand A. Eur. J. Org. Chem. 2008, 4567

<A NAME="RZ24210SS-7B">7b</A> Mitsudo K. Shiraga T. Tanaka H. Tetrahedron Lett. 2008, 49: 6593

<A NAME="RZ24210SS-8A">8a</A> Suzuki A. J. Organomet. Chem. 1999, 576: 147

<A NAME="RZ24210SS-8B">8b</A> Smith KA. Campi EM. Jackson WR. Marcuccio S. Naeslund CGM. Deacon GB. Synlett 1997, 131

<A NAME="RZ24210SS-9">9</A> Demir AS. Reis O. Emrullahoglu M. J. Org. Chem. 2003, 68: 10130

<A NAME="RZ24210SS-10">10</A> Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998, 39: 2937

<A NAME="RZ24210SS-11">11</A> Prokopcová H. Kappe CO. Angew. Chem. Int. Ed. 2009, 48: 2276

<A NAME="RZ24210SS-12">12</A> Zeng M. Du Y. Shao L. Qi C. Zhang X.-M. J. Org. Chem. 2010, 75: 2556

<A NAME="RZ24210SS-13">13</A> Courtois V. Barhdadi R. Troupel M. Perichon J. Tetrahedron 1997, 53: 11569

<A NAME="RZ24210SS-14">14</A> Hartmann CE. Nolan SP. Cazin CSJ. Organometallics 2009, 28: 2915

<A NAME="RZ24210SS-15">15</A> Nising CF. Schmid UK. Nieger M. Braese S. J. Org. Chem. 2004, 69: 6830

<A NAME="RZ24210SS-16">16</A> Dong D.-J. Li H.-H. Tian S.-K. J. Am. Chem. Soc. 2010, 132: 5018

<A NAME="RZ24210SS-17">17</A> Ma N. Zhu Z. Wu Y. Tetrahedron 2007, 63: 4625

<A NAME="RZ24210SS-18">18</A> Qi C. Sun X. Lu C. Yang J. Du Y. Wu H. Zhang X.-M. J. Organomet. Chem. 2009, 694: 2912

CuSO4-Mediated Homocoupling of Arylboronic Acids under Ligand- and Base-Free Conditions in Air

CuSO₄-Mediated Homocoupling of Arylboronic Acids under Ligand- and Base-Free Conditions in Air