FeCl2 Catalyzed Three-Component Reactions of Phospholes, Pyrrolidine, and Ketones (Aldehydes): Chemoselective Synthesis of 1‑Phosphafulvenes

FeCl2 Catalyzed Three-Component Reactions of Phospholes, Pyrrolidine, and Ketones (Aldehydes): Chemoselective Synthesis of 1‑Phosphafulvenes

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 2H-phospholes and [6 + 6] self-dimerization. The [6 + 4] and [6 + 6...

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Veröffentlicht in:Organic letters 2021-04, Vol.23 (8), p.2943-2947
Hauptverfasser: Liu, Yanjie, Fan, Xinran, Tian, Rongqiang, Duan, Zheng
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creator Liu, Yanjie
Fan, Xinran
Tian, Rongqiang
Duan, Zheng
description 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 2H-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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title FeCl2 Catalyzed Three-Component Reactions of Phospholes, Pyrrolidine, and Ketones (Aldehydes): Chemoselective Synthesis of 1‑Phosphafulvenes
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