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Selective Cyanoalkylation and [2+2+2] Annulation of 1,6‐Enynes with Azobis(alkylcarbonitriles) under Mild Conditions
Author(s) -
Kang QingQing,
Liu Yi,
Huang XunJie,
Li Qiang,
Wei WenTing
Publication year - 2019
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.201901483
Subject(s) - annulation , chemistry , regioselectivity , catalysis , reaction conditions , medicinal chemistry , organic chemistry , stereochemistry
In this paper, selective cyanoalkylation and [2+2+2] annulation of 1,6‐enynes with azobis(alkylcarbonitriles) under mild conditions is presented. When the reaction was run in EtOAc without any catalysts or additives, a highly regioselective cyanoalkylation of 1,6‐enynes was achieved. On the other hand, when a mixture of H 2 O and EtOAc was used as the green reaction medium in the presence of a cheap copper catalyst and an additive, a [2+2+2] annulation of 1,6‐enynes with azobis(isobutyronitrile) (AIBN) and H 2 O occurred to form four new chemical bonds in one step.