A Practical Preparation of 2-Carboxyphenylboronic Acid and its Application for the Preparation of Biaryl-2-carboxylic Acids using Suzuki Coupling Reactions

Bin Tao; Subhash C. Goel; Jagvir Singh; David W. Boykin

doi:10.1055/s-2002-31954

PAPER

A Practical Preparation of 2-Carboxyphenylboronic Acid and its Application for the Preparation of Biaryl-2-carboxylic Acids using Suzuki Coupling Reactions

Bin Tao^a, Subhash C. Goel^b, Jagvir Singh^b, David W. Boykin*^a
^a Department of Chemistry, Georgia State University, University Plaza, Atlanta, GA 30303, USA
Fax: +1(404)6511416; e-Mail: dboykin@gsu.edu;
^b Optima Chemical Group, LLC, 200 Willacoochee HWY, Douglas, GA 31533, USA

Abstract

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Abstract

A practical synthesis of 2-carboxyphenylboronic from 2-tolylboronic acid and aqueous potassium permanganate under mild conditions is reported. The title compound couples with aryl bromides containing electron-withdrawing groups to give biaryl-2-carboxylic acids.

Key words

2-carboxyphenylboronic acid - 2-tolylboronic acid - biaryl-2-carboxylic acids - Suzuki coupling - palladium catalyst

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References

1a For recent reviews, see: Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

1b Stanforth SP. Tetrahedron 1998, 54: 263

1c Suzuki A. J. Organomet. Chem. 1999, 576: 147

1d Buchwald SL. Fox JM. The Strem Chemiker 2000, 18: 1

1e Llord-Williams P. Giralt E. Chem. Soc. Rev. 2001, 30: 145

2a For recent examples, see: Dupuis C. Adiey K. Charruault L. Michelet V. Savignac M. Genet J.-P. Tetrahedron Lett. 2001, 42: 6523

2b Feuerstein M. Doucet H. Santelli M. Tetrahedron Lett. 2001, 42: 6667

2c Shaughnessy KH. Booth RS. Org. Lett. 2001, 3: 2757

2d Li GY. Angew. Chem., Int. Ed. 2001, 40: 1513

2e Bedford RB. Cazin CSJ. Chem. Commun. 2001, 1540

2f Vaz B. Rosana R. Nieto M. Paniello AI. de Lera AR. Tetrahedron Lett. 2001, 42: 7409

2g Wang W. Xiong C. Yang J. Hruby VJ. Tetrahedron Lett. 2001, 42: 7717

2h Zhuravel MA. Nguyen ST. Tetrahedron Lett. 2001, 42: 7925

2i Schomaker JM. Delia TJ. J. Org. Chem. 2001, 66: 7125

2j Netherton MR. Fu GC. Org. Lett. 2001, 3: 4295

2k Yin J. Rainka MP. Zhang X. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 1162

2l Molander GA. Rivero MR. Org. Lett. 2002, 4: 107

3 Bettman B. Branch GEK. J. Am. Chem. Soc. 1934, 56: 1616

4

Several commercial sources of 2-carboxylphenylboronic acid are available now, all of which appeared after completion of this work.

5a Moreno-Manas M. Perez M. Pleixats R. J. Org. Chem. 1996, 61: 2346

5b Wong MS. Zhang XL. Tetrahedron Lett. 2001, 42: 4087

6 Bell LN, Burke MT, Hodgson GL, and Shumaker TK. inventors; Eur. Pat. Appl. EP 59983. ; Chem. Abstr. 1983, 98, 106980

7 Wolfe JP. Singer RA. Yang BH. Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9550

8 Zhang C. Huang J. Trudell ML. Nolan SP. J. Org. Chem. 1999, 64: 3804

9 LeBlond CR. Andrews AT. Sun Y. Sowa JR. Tetrahedron Lett. 2001, 42: 1555

10 Dyer UC. Shapland PD. Tiffin PD. Tetrahedron Lett. 2001, 42: 1765

11 Gong Y. Pauls HW. Synlett 2000, 829

12 Li J. Serdyuk L. Ferraris DV. Xiao G. Tays KL. Kletzly PW. Li W. Lautar S. Zhang J. Kalish V. Bioorg. Med. Chem. Lett. 2001, 11: 1687

13 Neiswender DD. Moniz WB. Dixon JA. J. Am. Chem. Soc. 1960, 82: 2876

14 DeSchepper RE. Swenton JS. Tetrahedron Lett. 1985, 26: 4831

15 Glover GW. Goosen A. J. Chem. Soc., Perkin Trans.1 1978, 653

16 Rapoport H. Williams AR. J. Am. Chem. Soc. 1949, 71: 1774

17 Kenner GW. Murray MA. Tylor CMB. Tetrahedron 1957, 1: 259

18 Hey DH. Leonard JA. Rees CW. J. Chem. Soc. 1962, 4579