期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 9, 期 10, 页码 3005-3010出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201402643
关键词
alkynes; copper; regioselectivity; silicon; silylmetalation
资金
- NRW Graduate School of Chemistry
The copper(I) alkoxide-catalyzed release of a silicon-based cuprate reagent from a silicon-boron pronucleophile is applied to the addition across carbon-carbon triple bonds. Commercially available CuBrMe2S was found to be a general precatalyst that secures high regiocontrol for both aryl- and alkyl-substituted terminal as well as internal alkynes. The solvent greatly influences the regioisomeric ratio, favoring the linear regioisomer with terminal acceptors. This facile protocol even allows for the transformation of internal acceptors with remarkable levels of regio- and diastereocontrol.
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