Selective protodeboronation: synthesis of 4-methyl-2-thiopheneboronic anhydride and demonstration of its utility in Suzuki-Miyaura reactions

被引：23

作者：

Klingensmith, Liane M. ^{[1
]}

Bio, Matthew M. ^{[1
]}

Moniz, George A. ^{[1
]}

机构：

[1] Amgen Inc, Chem Proc R&D, Cambridge, MA 02139 USA

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 46期

关键词：

regioselective; lithiation; protodeboronation; Suzuki;

D O I：

10.1016/j.tetlet.2007.09.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of 4-methyl-2-thiopheneboronic anhydride is reported. Regioselective lithiation of 3-methylthiophene followed by reaction with triisopropylborate and hydrolysis provides a 92:8 ratio of 4-methyl-2-thiopheneboronic acid (1) and regioisomeric 2-methyl-3-thiopheneboronic acid (3). The undesired regioisomer is selectively protodeboronated with concentrated acid to provide only the desired 4-methyl-2-thiopheneboronic acid (1). The title compound is isolated by dehydration/crystallization and employed in several Suzuki-Miyaura reactions. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8242 / 8245

页数：4

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