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Issue 21, 2019
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A rhodium-catalyzed three-component reaction of arylisocyanides, trifluorodiazoethane, and activated methylene isocyanides or azomethine ylides: an efficient synthesis of trifluoroethyl-substituted imidazoles

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Abstract

A rhodium-catalyzed three-component reaction of isocyanides, 2,2,2-trifluorodiazoethane and activated methylene isocyanides or azomethine ylides has been developed. In this transformation, the ketenimine intermediates generated by the coupling reaction of arylisocyanides with 2,2,2-trifluorodiazoethane undergo intermolecular [3 + 2] cyclization with activated methylene isocyanides or azomethine ylides and provide a new and highly efficient method for the construction of trifluoroethyl-substituted imidazoles in a single step.

Graphical abstract: A rhodium-catalyzed three-component reaction of arylisocyanides, trifluorodiazoethane, and activated methylene isocyanides or azomethine ylides: an efficient synthesis of trifluoroethyl-substituted imidazoles

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Article information


Submitted
04 Jul 2019
Accepted
16 Sep 2019
First published
17 Sep 2019

Org. Chem. Front., 2019,6, 3657-3662
Article type
Research Article

A rhodium-catalyzed three-component reaction of arylisocyanides, trifluorodiazoethane, and activated methylene isocyanides or azomethine ylides: an efficient synthesis of trifluoroethyl-substituted imidazoles

Y. Yu, Y. Zhang, Z. Wang, Y. Liang and Y. Zhao, Org. Chem. Front., 2019, 6, 3657 DOI: 10.1039/C9QO00856J

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