Visible-Light-Driven Catalytic Alkylation of Reactive Alkyl Nitriles with Nonactivated Alkenes Using an Amine as a
Yuki Sato1, Tomoya Hisada1, Yasuhiro Yamashita1
1Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, Japan, 113-0033.
Abstract:
We have developed a photoinduced catalytic alkylation reaction of reactive alkyl nitriles with nonactivated alkenes using a simple amine as a hydrogen atom transfer (HAT) catalyst. This reaction proceeds smoothly under mild reaction conditions with blue LED irradiation to afford a variety of alkylated nitriles. Not only were unactivated alkenes employable but also styrene derivatives. The key to success of this reaction is the generation of an electrophilic alkyl radical species from alkyl nitrile. The use of a readily available amine catalyst such as N,N-dialkylanilines is effective to promote this reaction efficiently.
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