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
Current Organic Chemistry
Title:Synthesis of Aminophosphines and Their Applications in Catalysis
Volume: 16 Issue: 24
Author(s): Valeria A. Stepanova and Irina P. Smoliakova
Affiliation:
Keywords: C–P bond formation reactions, P, N-bidentate ligands, Aminophosphines, Ferrocene-based aminophosphines, Phosphinooxazolines, phosphinopyridines
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.
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Cite this article as:
A. Stepanova Valeria and P. Smoliakova Irina, Synthesis of Aminophosphines and Their Applications in Catalysis, Current Organic Chemistry 2012; 16 (24) . https://dx.doi.org/10.2174/138527212804546723
DOI https://dx.doi.org/10.2174/138527212804546723 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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