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Cyanomethylation of alkenes with C–H bond activation of acetonitrile: in situ generated diazonium salts as promoters without transition-metals

Author:
Ni, Zhangqin, Huang, Xin, Wang, Jichao, Pan, Yuanjiang
Source:
RSC advances 2015 v.6 no.1 pp. 522-526
ISSN:
2046-2069
Subject:
acetonitrile, alkenes, carbon-hydrogen bond activation, chemical bonding, diazonium compounds, moieties, nitrites, photocatalysts
Abstract:
Diazonium salts, which were in situ generated from p-anisidine and tert-butyl nitrite, could be used as a novel radical promoter for the Cₛₚ₃–H functionalization of acetonitrile. The cyanomethylation of alkenes could be performed without the use of transition-metal salts or photocatalyst and the functionalized oxindoles could be obtained with simple operation in moderate to good yields. This process tolerates a variety of functional groups and provides an alternative procedure for the synthesis of functionalized oxindoles.
Agid:
6401471