Metal-Free Generation of Phosphorus-Centered Radicals for the Synthesis of Phosphorus-Based Heterocycles: A Personal Account

Valentin Quint; Ludovik Noël-Duchesneau; Elodie Lagadic; Fabrice Morlet-Savary; Jacques Lalevée; Annie- Claude Gaumont; Sami Lakhdar

doi:10.1055/s-0036-1588499

Synthesis, Table of Contents

Synthesis 2017; 49(15): 3444-3452
DOI: 10.1055/s-0036-1588499

short review

Metal-Free Generation of Phosphorus-Centered Radicals for the Synthesis of Phosphorus-Based Heterocycles: A Personal Account

Valentin Quint

^aNormandie Université, Laboratoire de Chimie Moléculaire et Thio-organique, CNRS-UMR 6507, ENSICAEN, Université de Caen Normandie, 6 Boulevard du Maréchal Juin, 14000 Caen, France Email: Sami.lakhdar@ensicaen.fr

,

Ludovik Noël-Duchesneau

^aNormandie Université, Laboratoire de Chimie Moléculaire et Thio-organique, CNRS-UMR 6507, ENSICAEN, Université de Caen Normandie, 6 Boulevard du Maréchal Juin, 14000 Caen, France Email: Sami.lakhdar@ensicaen.fr

,

Elodie Lagadic

^aNormandie Université, Laboratoire de Chimie Moléculaire et Thio-organique, CNRS-UMR 6507, ENSICAEN, Université de Caen Normandie, 6 Boulevard du Maréchal Juin, 14000 Caen, France Email: Sami.lakhdar@ensicaen.fr

,

Fabrice Morlet-Savary

^bInstitut de Science des Matériaux de Mulhouse IS2M, UMR CNRS 7361, UHA, 15 rue Jean Starcky, 68057 Mulhouse Cedex, France

,

Jacques Lalevée

^bInstitut de Science des Matériaux de Mulhouse IS2M, UMR CNRS 7361, UHA, 15 rue Jean Starcky, 68057 Mulhouse Cedex, France

,

Annie- Claude Gaumont

^aNormandie Université, Laboratoire de Chimie Moléculaire et Thio-organique, CNRS-UMR 6507, ENSICAEN, Université de Caen Normandie, 6 Boulevard du Maréchal Juin, 14000 Caen, France Email: Sami.lakhdar@ensicaen.fr

,

Sami Lakhdar*

^aNormandie Université, Laboratoire de Chimie Moléculaire et Thio-organique, CNRS-UMR 6507, ENSICAEN, Université de Caen Normandie, 6 Boulevard du Maréchal Juin, 14000 Caen, France Email: Sami.lakhdar@ensicaen.fr

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Abstract

All articles of this category

Dedicated to Prof. Herbert Mayr on the occasion of his 70^th birthday

Abstract

This short review describes our recent efforts to generate phosphorus-based radicals under metal-free conditions and their use as key intermediates for the synthesis of phosphorus-based heterocycles. In this regard, the synthesis of benzo[b]phosphole oxides and 6-phosphorylated phenanthridines will be reported. While the synthesis of the former lies in the use of photoredox catalysis, the latter have been obtained through the use of an electron donor–acceptor complex from the combination of diphenyliodonium ion with triethylamine. Mechanistic aspects of both reaction types are discussed based on detailed mechanistic studies including electron paramagnetic resonance, UV–vis spectroscopic, NMR and steady-state photolysis experiments.

1 Introduction

2 Photoredox Catalysis for the Generation of Phosphinoyl Radicals

3 Generation of Phosphinoyl Radicals through the Formation of EDA Complexes

4 Conclusions

Key words

phosphorus - photochemistry - electron transfer - radical reaction

Full Text

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