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Metal‐Free Coupling of 3‐Alkenyl Oxoindoles by Nucleophilic Vinylic Substitution of Nitroolefins
Author(s) -
Zhang Hongrui,
Liu Yun,
Chen Rui,
Xue Jijun,
Li Ying,
Tang Yu
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300032
Subject(s) - chemistry , nucleophile , nucleophilic substitution , nitro , nucleophilic aromatic substitution , organic chemistry , substitution reaction , combinatorial chemistry , catalysis , alkyl
The fuge‐es : A metal‐free coupling reaction for the synthesis of oxindoles by nucleophilic vinylic substitution (S N V) of nitroolefins is described. By using the nitro group as a nucleofuge, the reaction proceeds through a Michael addition/1,2‐ cis ‐elimination process. Alcohols, phenols, amines, thiols, and even a β‐ketoester worked as nucleophiles to form CO, CN, CS, and CC bonds and afford the corresponding oxindoles.