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
收藏
页码：4661 / 4671
页数：11
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