- Heteroatom-directed alkylcyanation of alkynes
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Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the γ-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 β-hydride elimination to allow the alkylcyanation reaction.
- Nakao, Yoshiaki,Yada, Akira,Hiyama, Tamejiro
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supporting information; experimental part
p. 10024 - 10026
(2010/10/04)
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