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Synthesis of Branched Alkylboronates by Copper‐Catalyzed Allylic Substitution Reactions of Allylic Chlorides with 1,1‐Diborylalkanes
Author(s) -
Kim Junghoon,
Park Sangwoo,
Park Jinyoung,
Cho Seung Hwan
Publication year - 2016
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.201509840
Subject(s) - allylic rearrangement , imes , chemistry , catalysis , substitution reaction , copper , medicinal chemistry , imidazole , stereochemistry , organic chemistry , carbene
Reported herein is a copper‐catalyzed S N 2′‐selective allylic substitution reaction using readily accessible allylic chlorides and 1,1‐diborylalkanes, a reaction which proceeds with chemoselective C−B bond activation of the 1,1‐diborylalkanes. In the presence of a catalytic amount of [Cu(IMes)Cl] [IMes=1,3‐bis(2,4,6‐trimethylphenyl)imidazole‐2‐ylidene] and LiO t Bu as a base, a range of primary and secondary allylic chlorides undergo the S N 2′‐selective allylic substitution reaction to produce branched alkylboronates. The synthetic utilities of the obtained alkylboronates are also presented.