Synthesis
DOI: 10.1055/a-1511-0382
short review

Nucleophilic H-Phosphites, H-Phosphinates, and H-Phosphine Oxides in Organic Reactions

Zhan-Yong Wang
,
Qi Guo
,
Shaohong Xu
,
We thank the National Natural Science Foundation of China (21801214), Foundation of University Student Innovation Program (S202011071012).


Abstract

P(O)–H compounds like H-phosphites, H-phosphinates, and H-phosphine oxides are widely used as nucleophiles. Herein, their reactions with unsaturated compounds, C–H activation, the Hirao reaction, P–C, P–S, P–O, P–N, and P–F couplings are thoroughly discussed and summarized. This review will focus on their reactions with alkenes, alkynes, enamides, propynoic acids, epoxide, arynes, arenes, quinones, isothiocyanates, diazo compounds, aldehydes, ketones, imines, pyridines, acid derivatives, carbocations, aryl halides, dibromoalkenes, disulfides, thiosulfates, sulfonyl chlorides, iodonium salts, amines, alcohols, and thiols.

1 Introduction

2 Addition to Alkenes/Alkynes

3 Addition to Other Unsaturated Compounds

4 Coupling with Carbocations

5 Phosphorylation of Aryl C–H Bonds

6 Hirao Reaction

7 P–S, P–O, P–N, or P–F Coupling

8 Conclusions



Publication History

Received: 17 May 2021

Accepted: 18 May 2021

Publication Date:
18 May 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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