Mild Silver(I)-Mediated Regioselective Iodination and Bromination of Arylboronic Acids

被引：57

作者：

Al-Zoubi, Raed M. ^{[1
]}

Hall, Dennis G. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Gunning Lemieux Chem Ctr, Edmonton, AB T6G 2G2, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 11期

基金：

加拿大自然科学与工程研究理事会;

关键词：

CROSS-COUPLING REACTIONS; PHASE-SWITCH SYNTHESIS; BORONIC ACIDS; CARBOXYLIC-ACIDS; PRODUCTIVE TAGS; ONYCHOMYCOSIS; FLUORINATION; HALOARENES; DISCOVERY; TRANSPORT;

D O I：

10.1021/ol100537x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and regioselective silver(I)-mediated electrophilic iodination and bromination reaction of arylboronic acids has been developed. The boronic acid does not require protection prior to the reaction, which can be performed on a multigram scale with moderate to excellent yields. A mild, simple, and effective method is disclosed to provide ortho-haloarylboronic acids that can be used as useful intermediates in selective sequential Suzuki-Miyaura cross-coupling reactions to provide ortho-triaryl derivatives in good yields.

引用

页码：2480 / 2483

页数：4

共 37 条

[1] Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature [J].

Al-Zoubi, Raed M. ;

Marion, Olivier ;

Hall, Dennis G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2876-2879

[2] Cavitand boronic acids mediate highly selective fructose transport [J].

Altamore, TM ;

Barrett, ES ;

Duggan, PJ ;

Sherburn, MS ;

Szydzik, ML .

ORGANIC LETTERS, 2002, 4 (20) :3489-3491

[3] Synthesis, evaluation and application of novel bifunctional N,N-di-isopropylbenzylamineboronic acid catalysts for direct amide formation between carboxylic acids and amines [J].

Arnold, Kenny ;

Batsanov, Andrei S. ;

Davies, Bryan ;

Whiting, Andrew .

GREEN CHEMISTRY, 2008, 10 (01) :124-134

[4] Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2690), for the potential treatment of onychomycosis [J].

Baker, Stephen J. ;

Zhang, Yong-Kang ;

Akama, Tsutomu ;

Lau, Agnes ;

Zhou, Huchen ;

Hernandez, Vincent ;

Mao, Weimin ;

Alley, M. R. K. ;

Sanders, Virginia ;

Plattner, Jacob J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (15) :4447-4450

[5] Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters [J].

Beenen, Melissa A. ;

Weix, Daniel J. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6304-6305

[6] Metal-free electrophilic fluorination of alkyl trifluoroborates and boronic acids [J].

Cazorla, Clement ;

Metay, Estelle ;

Andrioletti, Bruno ;

Lemaire, Marc .

TETRAHEDRON LETTERS, 2009, 50 (27) :3936-3938

[7] Probing Intramolecular B-N Interactions in Ortho-Aminomethyl Arylboronic Acids [J].

Collins, Byron E. ;

Sorey, Steven ;

Hargrove, Amanda E. ;

Shabbir, Shagufta H. ;

Lynch, Vincent M. ;

Anslyn, Eric V. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) :4055-4060

[8] Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].

Constable, David J. C. ;

Dunn, Peter J. ;

Hayler, John D. ;

Humphrey, Guy R. ;

Leazer, Johnnie L., Jr. ;

Linderman, Russell J. ;

Lorenz, Kurt ;

Manley, Julie ;

Pearlman, Bruce A. ;

Wells, Andrew ;

Zaks, Aleksey ;

Zhang, Tony Y. .

GREEN CHEMISTRY, 2007, 9 (05) :411-420

[9] Palladium-mediated fluorination of arylboronic acids [J].

Furuya, Takeru ;

Kaiser, Hanns Martin ;

Ritter, Tobias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (32) :5993-5996

[10] Fluorination of Boronic Acids Mediated by Silver(I) Triflate [J].

Furuya, Takeru ;

Ritter, Tobias .

ORGANIC LETTERS, 2009, 11 (13) :2860-2863

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