Modular Approach to Reductive Csp2-H and Csp3-H Silylation of Carboxylic Acid Derivatives through Single-Pot, Sequential Transition Metal Catalysis

被引：26

作者：

Hua, Yuanda ^{[1
]}

Jung, Seongjeong ^{[1
]}

Roh, James ^{[1
]}

Jeon, Junha ^{[1
]}

机构：

[1] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 09期

关键词：

C-H SILYLATION; CROSS-COUPLING REACTIONS; CARBONYL-COMPOUNDS; REGIOSELECTIVE SILYLATION; BOND FUNCTIONALIZATION; SILICON ISOSTERES; HYDROSILYLATION; RUTHENIUM; ESTERS; ARENES;

D O I：

10.1021/acs.joc.5b00564

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a modular approach to catalytic reductive C-sp2-H and C-sp3-H silylation of carboxylic acid derivatives encompassing esters, ketones, and aldehydes. Choice of either an Ir(I)/Rh(I) or Rh(I)/Rh(I) sequence leads to either exhaustive reductive ester or reductive ketone/aldehyde silylation, respectively. Notably, a catalyst-controlled direct formation of doubly reduced silyl ethers is presented, specifically via Ir-catalyzed exhaustive hydrosilylation. The resulting silyl ethers undergo C-sp2-H and benzylic C-sp3-H silylation in a single vessel.

引用

页码：4661 / 4671

页数：11

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