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

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-trifluorodiazoeth...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 21; pp. 3657 - 3662
Main Authors Yu, Yang, Zhang, Yan, Wang, Zhuo, Liang, Yong-Xin, Zhao, Yu-Long
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.11.2019
Royal Society of Chemistry
Subjects
Catalysis
Chemistry
Chemistry, Organic
Crystallography
Intermediates
Methylene
Organic chemistry
Physical Sciences
Rhodium
Science & Technology
Substitutes
ALPHA-DIAZO COMPOUNDS
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
ONE-POT SYNTHESIS
PROPARGYL AMIDINES
H BOND FUNCTIONALIZATION
3+2 CYCLOADDITION
ACCESS
N-TOSYLHYDRAZONES
TRIFLUOROMETHYLATION
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Summary: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.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c9qo00856j