期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 52, 页码 15876-15879出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508181
关键词
C-H activation; electrophilic substitution; hydrosilylation; N-heterocycles; Si-H bond activation
资金
- Deutsche Forschungsgemeinschaft [Oe 249/10-1]
- Einstein Foundation (Berlin)
A C-H silylation of pyridines that seemingly proceeds through electrophilic aromatic substitution (SEAr) is reported. Reactions of 2- and 3-substituted pyridines with hydrosilanes in the presence of a catalyst that splits the Si-H bond into a hydride and a silicon electrophile yield the corresponding 5-silylated pyridines. This formal silylation of an aromatic C-H bond is the result of a three-step sequence, consisting of a pyridine hydrosilylation, a dehydrogenative C-H silylation of the intermediate enamine, and a 1,4-dihydropyridine retro-hydrosilylation. The key intermediates were detected by H-1 NMR spectroscopy and prepared through the individual steps. This complex interplay of electrophilic silylation, hydride transfer, and proton abstraction is promoted by a single catalyst.
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