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FeCl Catalyzed Three-Component Reactions of Phospholes, Pyrrolidine, and Ketones (Aldehydes): Chemoselective Synthesis of 1-Phosphafulvenes. | LitMetric

FeCl Catalyzed Three-Component Reactions of Phospholes, Pyrrolidine, and Ketones (Aldehydes): Chemoselective Synthesis of 1-Phosphafulvenes.

Org Lett

College of Chemistry, Green Catalysis Center, International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, Zhengzhou University, Zhengzhou 450001, PR China.

Published: April 2021

We have developed an unprecedented approach for the synthesis of transient 1-phosphafulvenes through three component reactions of phospholes. The generation of 1-phosphafulvenes was demonstrated by in situ [6 + 4] cycloaddition with 2-phospholes and [6 + 6] self-dimerization. The [6 + 4] and [6 + 6] reaction pathway could be modulated by the starting ketones and aldehydes. The construction of 1-phosphafulvenes is illustrated by a proposed mechanism combining nucleophilic addition of phospholide to the iminium or isomerized azomethine ylide and a [1,5]-shift of phosphole.

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http://dx.doi.org/10.1021/acs.orglett.1c00602DOI Listing

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