Recent progress in reactivity study and synthetic application of N-heterocyclic phosphorus hydrides

Author:

Zhang Jingjing1,Yang Jin-Dong1ORCID,Cheng Jin-Pei12

Affiliation:

1. Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, China

2. State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

Abstract

Abstract N-heterocyclic phosphines (NHPs) have recently emerged as a new group of promising catalysts for metal-free reductions, owing to their unique hydridic reactivity. The excellent hydricity of NHPs, which rivals or even exceeds those of many metal-based hydrides, is the result of hyperconjugative interactions between the lone-pair electrons on N atoms and the adjacent σ*(P–H) orbital. Compared with the conventional protic reactivity of phosphines, this umpolung P–H reactivity leads to hydridic selectivity in NHP-mediated reductions. This reactivity has therefore found many applications in the catalytic reduction of polar unsaturated bonds and in the hydroboration of pyridines. This review summarizes recent progress in studies of the reactivity and synthetic applications of these phosphorus-based hydrides, with the aim of providing practical information to enable exploitation of their synthetically useful chemistry.

Funder

National Natural Science Foundation of China

National Science Foundation

Publisher

Oxford University Press (OUP)

Subject

Multidisciplinary

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