期刊
ACS CATALYSIS
卷 7, 期 12, 页码 8171-8175出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03056
关键词
gamma-C-H activation; silylation; germanylation; organopalladium aystal; mechanistic studies; DFT
资金
- SERB [EMR/2015/000164]
- CSIR-India
- UGC-India
- IITB
- SERB
- SpaceTime supercomputing facility
A Pd(II)-catalyzed protocol for highly regioselective distal gamma-C-H silylation and germanylation of aliphatic carboxylic acids is reported. Bidentate 8-aminoquinoline as the directing group was found to stabilize the six-membered palladacycle. A variety of aliphatic carboxylic acids and amino acids were silylated and germanylated in good yields and high diasteroselectivities. Detailed mechanistic studies involving isolation of a Pd(II) intermediate, determination of the reaction rate and order, control experiments, and isotopic labeling and DFT studies were found to be crucial for elucidating the elementary steps involved in this distal aliphatic functionalization.
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