期刊
ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 2, 期 11, 页码 968-976出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201300164
关键词
carbometalation; cross-coupling; nickel; organoboronic acids; trans-addition
资金
- MEXT
Cyclizative alkynylboration and alkenylboration of carbon-carbon triple bonds proceeds in the presence of a nickel catalyst. Chloroboranes bearing homopropargyloxy or bishomopropargyloxy groups were used as substrates with alkynylstannane, vinylstannane, and alkenylzirconium reagents as donors of organic groups. The reaction mechanism may involve the following elementary steps: oxidative addition of the B-Cl bond to a nickel(0) catalyst, insertion of the triple bond into the Ni-B bond, Z-to-E isomerization of the alkenylnickel intermediate, transmetalation from organostannane or organozirconium reagents, and reductive elimination of the B-C bond. An intermediary nickel complex was isolated and identified by a single-crystal X-ray analysis.
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