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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Synthesis of Aminophosphines and Their Applications in Catalysis

Author(s): Valeria A. Stepanova and Irina P. Smoliakova

Volume 16, Issue 24, 2012

Page: [2893 - 2920] Pages: 28

DOI: 10.2174/138527212804546723

Abstract

The review describes preparation of P,N-bidentate ligands without a P–N bond and their use in asymmetric catalysis. Diverse types of aminophosphines are considered with emphasis on P,N-ferrocene ligands, phosphino-oxazolines and phosphinopyridines. The following major synthetic approaches to aminophosphines and related compounds are summarized: (i) via lithiation, (ii) the use of Grignard reagents, (iii) nucleophilic substitution using metal phosphides, (iv) Staudinger method, (v) hydrophosphination of α,β-unsaturated carbonyl compounds, (vi) Cu- and Pd-catalyzed C–P bond formation reactions, and (vii) reactions of cyclopalladated complexes with metal phosphides and HPPh2. Highlights of aminophosphine applications in asymmetric synthesis include their use in hydrogenation, hydrosilylation, and hydroboration reactions as well as in various transformations leading to a C–C bond formation such as Suzuki coupling, Meerwein-Eschenmoser-Claisen rearrangement, Mukaiyama aldol reaction, Tsuji allylation and ethylene oligomerization.

Keywords: C–P bond formation reactions, P, N-bidentate ligands, Aminophosphines, Ferrocene-based aminophosphines, Phosphinooxazolines, phosphinopyridines

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