Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 Japan.
Org Lett. 2011 Sep 2;13(17):4656-9. doi: 10.1021/ol2018664. Epub 2011 Aug 1.
A silver-catalyzed carbomagnesiation of alkynes with alkyl halides and Grignard reagents afforded alkenyl Grignard reagents regioselectively, where the alkyl group of the alkyl halide, but not that of the Grignard reagent, was introduced into the alkyne. Application to δ-haloalkylacetylenes yielded cyclopentanes or a tetrahydrofuran containing an exo-methylene substituent via 5-exo-dig cyclization.
银催化炔烃与卤代烃和格氏试剂的碳镁化反应，以区域选择性的方式得到烯基格氏试剂，其中卤代烃的烷基取代基，但不是格氏试剂的烷基取代基，被引入到炔烃中。应用于δ-卤代炔烃，通过 5-endo-dig 环化反应生成含有反式亚甲基取代基的环戊烷或四氢呋喃。
