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Synthesis 2017; 49(21): 4783-4807
DOI: 10.1055/s-0036-1588542
short review
© Georg Thieme Verlag Stuttgart · New York

Catalyst- and Solvent-Free Addition of the P–H Species to Alkenes and Alkynes: A Green Methodology for C–P Bond Formation

Nina K. Gusarova
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
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Nataliya A. Chernysheva
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
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Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
› Author AffiliationsThis study was performed under financial support by the Council for Grants at the President of the Russian Federation (project no. NSh-7145.2016.3).
Further Information

Publication History

Received: 25 May 2017

Accepted after revision: 18 July 2017

Publication Date:
28 August 2017 (online)

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Abstract

Traditional methods for C–P bond formation via direct addition of P–H species to unsaturated compounds are usually implemented in the presence of base and metal catalysts or radical initiators in various organic solvents. During the last five years, a novel efficient and general catalyst/initiator- and solvent-free version of the hydrophosphination and hydrophosphinylation of multiple C–C bonds with H-phosphines and their chalcogenides has begun to develop and it is attracting growing attention. This approach corresponds to the recently emerged pot-, atom-, and step-economy (PASE) green paradigm. This review covers the literature on the synthesis of useful and in-demand organophosphorus compounds via catalyst- and solvent-free addition of P–H species to alkenes and alkynes.

1 Introduction

2 Addition of Secondary Phosphines to Alkenes

3 Hydrophosphinylation of Alkenes with Secondary Phosphine Chalcogenides

3.1 Oxidative Addition of Phosphine Oxides to Vinyl Sulfides

3.2 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Alkenes

3.3 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Divinyl Chalcogenides

3.4 Hydrophosphinylation of Alkenes with Secondary Phosphine/Chalcogen Pair (Three-Component Reactions)

4 Addition of Secondary Phosphines to Alkynes

5 Addition of Secondary Phosphine Chalcogenides to Alkynes

6 Conclusion

Key words

catalyst-free - solvent-free - hydrophosphination - hydrophosphinylation - phosphine oxides - phosphine sulfides - phosphine selenides - green chemistry