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C ‐Propargylation Overrides O ‐Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium‐Catalyzed Transfer Hydrogenation
Author(s) -
Liang Tao,
Woo Sang Kook,
Krische Michael J.
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.201603575
Subject(s) - rhodium , alkylation , chemistry , propargyl , halide , catalysis , alkyl , transfer hydrogenation , chloride , medicinal chemistry , organic chemistry , ruthenium
The canonical S N 2 behavior displayed by alcohols and activated alkyl halides in basic media (O‐alkylation) is superseded by a pathway leading to carbinol C‐alkylation under the conditions of rhodium‐catalyzed transfer hydrogenation. Racemic and asymmetric propargylations are described.