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C–H‐Alkenylation of Arenes in a One‐Pot VNS – Julia‐Kocienski Reaction
Author(s) -
Loska Rafał
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801018
Subject(s) - chemistry , carbanion , sulfone , nucleophile , trifluoromethyl , selectivity , nucleophilic aromatic substitution , sequence (biology) , nucleophilic substitution , nucleophilic addition , medicinal chemistry , organic chemistry , stereochemistry , catalysis , alkyl , biochemistry
A one‐pot reaction sequence is reported that enables direct introduction of alkenyl substituents into C–H positions of electron‐poor aromatic compounds under transition metal free conditions. The process incorporates vicarious nucleophilic substitution of hydrogen with carbanion of benzotriazolyl chloromethyl sulfone, followed by Julia‐Kocienski olefination with aliphatic or aromatic aldehydes or trifluoromethyl ketones. The resulting nitrostyrene derivatives are usually formed with very high E/Z selectivity.