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Cobalt‐Catalyzed Reductive Dimethylcyclopropanation of 1,3‐Dienes
Author(s) -
Werth Jacob,
Uyeda Christopher
Publication year - 2018
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.201807542
Subject(s) - cobalt , carbenoid , regioselectivity , cycloaddition , catalysis , reagent , chemistry , diene , yield (engineering) , combinatorial chemistry , transition metal , medicinal chemistry , organic chemistry , rhodium , materials science , natural rubber , metallurgy
Dimethylcyclopropanes are valuable synthetic targets that are challenging to access in high yield using Zn carbenoid reagents. Herein, we describe a cobalt‐catalyzed variant of the Simmons–Smith reaction that enables the efficient dimethylcyclopropanation of 1,3‐dienes using a Me 2 CCl 2 /Zn reagent mixture. The reactions proceed with high regioselectivity based on the substitution pattern of the 1,3‐diene. The products are vinylcyclopropanes, which serve as substrates for transition‐metal‐catalyzed ring‐opening reactions, including 1,3‐rearrangement and [5+2] cycloaddition. Preliminary studies indicate that moderately activated monoalkenes are also amenable to dimethylcyclopropanation under the conditions of cobalt catalysis.