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C−C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO t Bu: Unusual Regioselectivity through a Radical Mechanism
Author(s) -
Kumar Amit,
Janes Trevor,
Chakraborty Subrata,
Daw Prosenjit,
von Wolff Niklas,
Carmieli Raanan,
DiskinPosner Yael,
Milstein David
Publication year - 2019
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.201812687
Subject(s) - regioselectivity , chemistry , catalysis , medicinal chemistry , benzyl alcohol , alkylation , reaction mechanism , alcohol , photochemistry , organic chemistry
We report a C−C bond‐forming reaction between benzyl alcohols and alkynes in the presence of a catalytic amount of KO t Bu to form α‐alkylated ketones in which the C=O group is located on the side derived from the alcohol. The reaction proceeds under thermal conditions (125 °C) and produces no waste, making the reaction highly atom efficient, environmentally benign, and sustainable. Based on our mechanistic investigations, we propose that the reaction proceeds through radical pathways.