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Nickel‐Catalyzed Allylic Substitution of Simple Alkenes
Author(s) -
Matsubara Ryosuke,
Jamison Timothy F.
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000875
Subject(s) - allylic rearrangement , nickel , catalysis , phosphine , chemistry , trifluoromethanesulfonate , diene , silylation , selectivity , stoichiometry , substitution (logic) , substitution reaction , organic chemistry , combinatorial chemistry , natural rubber , computer science , programming language
This report describes a nickel‐catalyzed allylic substitution process of simple alkenes whereby an important structural motif, a 1,4‐diene, was prepared. The key to success is the use of an appropriate nickel–phosphine complex and a stoichiometric amount of silyl triflate. Reactions of 1‐alkyl‐substituted alkenes consistently provided 1,1‐disubstituted alkenes with high selectivity. Insight into the reaction mechanism as well as miscellaneous application of the developed catalytic process is also documented.