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Synthesis of 2,3,3a,4,5,6‐Hexahydrobenzo[b]thiophene‐3a‐carbaldehydes via a Tandem Reaction of Cyclic β‐Thiocyanatoenals with Electron‐Deficient Alkenes Triggered by Fluoride
Author(s) -
Zhang Min,
Gong Yuefa
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2115
Subject(s) - chemistry , thiophene , deprotonation , fluoride , yield (engineering) , tandem , medicinal chemistry , nucleophile , cascade reaction , sulfur , photochemistry , organic chemistry , catalysis , inorganic chemistry , ion , composite material , materials science , metallurgy
New hexahydrobenzo[b]thiophene derivatives 3 were conveniently synthesized by a fluoride‐promoted tandem reaction between cyclic β‐thiocyanatoenals 1 and terminal electron‐deficient alkenes 2 in low to moderate yield. The reaction was initiated by γ‐deprotonation and followed by the Michael addition and nucleophilic attack on sulfur center.