One-Pot Homologation of Boronic Acids: A Platform for Diversity-Oriented Synthesis

被引：31

作者：

Muir, Calum W. ^{[1
]}

Vantourout, Julien C. ^{[1
,2
]}

Isidro-Llobet, Albert ^{[2
]}

Macdonald, Simon J. F. ^{[2
]}

Watson, Allan J. B. ^{[1
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland

[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

C-H BORYLATION; PALLADIUM-CATALYZED BORYLATION; SMALL-MOLECULE SYNTHESIS; CROSS-COUPLING MODULES; BUILDING-BLOCKS; ARYL CHLORIDES; SPECIATION CONTROL; DERIVATIVES; ESTERS; ARENES;

D O I：

10.1021/acs.orglett.5b03030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formal homologation of sp(2)-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.

引用

页码：6030 / 6033

页数：4

共 60 条

[51] Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation [J].

Wang, Guanghui ;

Xu, Liang ;

Li, Pengfei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (25) :8058-8061

[52] Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction [J].

Woerly, Eric M. ;

Roy, Jahnabi ;

Burke, Martin D. .

NATURE CHEMISTRY, 2014, 6 (06) :484-491

[53] Stereoretentive Suzuki-Miyaura Coupling of Haloallenes Enables Fully Stereocontrolled Access to (-)-Peridinin [J].

Woerly, Eric M. ;

Cherney, Alan H. ;

Davis, Erin K. ;

Burke, Martin D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) :6941-+

[54] Direct introduction of a naphthalene-1,8-diamino boryl [B(dan)] group by a Pd-catalysed selective boryl transfer reaction [J].

Xu, Liang ;

Li, Pengfei .

CHEMICAL COMMUNICATIONS, 2015, 51 (26) :5656-5659

[55] Differentiated Di- and Polyboron Compounds: Synthesis and Application in Successive Suzuki-Miyaura Coupling [J].

Xu, Liang ;

Li, Pengfei .

SYNLETT, 2014, 25 (13) :1799-1802

[56] Site-Differentiated Polyboron Arenes Prepared by Direct C-H Borylation and Their Highly Selective Suzuki-Miyaura Cross-Coupling Reactions [J].

Xu, Liang ;

Ding, Siyi ;

Li, Pengfei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) :1822-1826

[57] NiCl2(PMe3)2-Catalyzed Borylation of Aryl Chlorides [J].

Yamamoto, Tetsuya ;

Morita, Tomoyuki ;

Takagi, Jun ;

Yamakawa, Tetsu .

ORGANIC LETTERS, 2011, 13 (21) :5766-5769

[58] Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis [J].

Yamashita, Yohei ;

Tellis, John C. ;

Molander, Gary A. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2015, 112 (39) :12026-12029

[59] Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates [J].

Yuen, AKL ;

Hutton, CA .

TETRAHEDRON LETTERS, 2005, 46 (46) :7899-7903

[60]

Zhang L.-S., 2014, Angew. Chem. Int. Ed Engl, V126, P3980

← 1 2 3 4 5 6 →