Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters

被引：25
|
作者：
Haydl, Alexander M. [1 ,2 ]
Hartwig, John F. [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] BASF SE, Carl Bosch Str 38, D-67056 Ludwigshafen, Germany
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 05期
关键词：
C-H BONDS; LATE-STAGE FUNCTIONALIZATION; NUCLEOPHILIC CHARACTER; ORTHO-METALATION; SUZUKI REACTIONS; CROSS-COUPLINGS; ALKYL RADICALS; DERIVATIVES; ACTIVATION; INHIBITORS;
D O I：
10.1021/acs.orglett.9b00025
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinyl-boronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.
引用
收藏
页码：1337 / 1341
页数：5
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