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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201603575
Subject(s) - rhodium , alkylation , chemistry , halide , propargyl , catalysis , alkyl , transfer hydrogenation , chloride , medicinal chemistry , organic chemistry , ruthenium
Abstract The canonical S N 2 behavior displayed by alcohols and activated alkyl halides in basic media (O‐alkylation) is superseded by a pathway leading to carbinol C‐alkylation under the conditions of rhodium‐catalyzed transfer hydrogenation.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.