Benchmarking Methanophosphocines as Versatile PIII/PV Redox Organocatalysts

Author:

Mele Lucas1,El Bekri Saudain Raphael1,Pirat Jean‐Luc1,Tomás‐Mendivil Eder2,Martin David2,Virieux David1,Ayad Tahar1

Affiliation:

1. ICGM Univ Montpellier CNRS ENSCM Montpellier France

2. Département de Chimie Moléculaire Université Grenoble Alpes 301 Rue de la Chimie Grenoble France

Abstract

AbstractPIII/PV redox cycling has recently emerged as a valuable strategy to minimized the chemical waste generated by phosphine‐mediated reaction, as well as enabling asymmetric transformation. In this article, we detail our contribution to this field by designing a series of diversely functionalized, electron‐rich bridgehead phosphine oxides with structural features that make them well‐suited as PIII/PV redox organocatalysts. Their catalytic performance has been assessed in various model reactions, including Wittig or Staudinger reactions, along with the reduction of activated alkenes and allenes. For each of these scenarios, we performed a comparative analysis with existing catalysts in order to demonstrate the applicability and limitation of methanophosphocines.

Publisher

Wiley

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