期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 29, 页码 10024-10026出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja1017078
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资金
- MEXT
- General Sekiyu Research & Development Encouragement & Assistance Foundation
- JSPS
- Grants-in-Aid for Scientific Research [21685023] Funding Source: KAKEN
Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the gamma-position are found to add across alkynes stereo- and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing beta-hydride elimination to allow the alkylcyanation reaction.
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