[1+1+1] Cyclotrimerization for the Synthesis of Cyclopropanes.
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Peer-reviewed
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Authors
Antonchick, Andrey P
Abstract
The synthesis of small rings by functionalization of C(sp(3) )-H bonds remains a great challenge. We report for the first time a copper-catalyzed [1+1+1] cyclotrimerization of acetophenone derivatives under mild reaction conditions. The reaction has a broad scope for the stereoselective synthesis of cyclopropanes by trimerization of acetophenone. The developed transformation is based on an extraordinary copper-catalyzed cascade process that allows saturated carbocycles to be obtained for the first time by cyclotrimerization through functionalization of C(sp(3) )-H bonds. The cascade of sixfold C(sp(3) )-H bond functionalization allows the synthesis of cyclopropanes in a highly stereoselective approach.
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Keywords
copper, cyclopropanes, cyclotrimerization, oxidative coupling, radicals
Journal Title
Angew Chem Int Ed Engl
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Journal ISSN
1433-7851
1521-3773
1521-3773
Volume Title
55
Publisher
Wiley