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Nickel‐Catalyzed Allylmethylation of Alkynes with Allylic Alcohols and AlMe 3 : Facile Access to Skipped Dienes and Trienes
Author(s) -
Li Wanfang,
Yu Shun,
Li Jincan,
Zhao Yu
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202006322
Subject(s) - allylic rearrangement , transmetalation , triphenylphosphine , reagent , alkene , catalysis , nickel , stereoselectivity , chemistry , alkyne , organic chemistry , combinatorial chemistry
We present herein an unprecedented allylative dicarbofunctionalization of alkynes with allylic alcohols. This simple catalytic procedure utilizes commercially available Ni(COD) 2 , triphenylphosphine, and inexpensive reagents, and delivers valuable skipped dienes and trienes with an all‐carbon tetrasubstituted alkene unit in a highly stereoselective fashion. Preliminary mechanistic studies support the reaction pathway of allylnickelation followed by transmetalation in this dicarbofunctionalization of alkynes.