Literature DB >> 24039197

Organophosphorus catalysis to bypass phosphine oxide waste.

Henri A van Kalkeren1, Floris L van Delft, Floris P J T Rutjes.   

Abstract

The conversion of oxygen-containing compounds is often achieved by the use of phosphorus reagents. The newly formed phosphine oxide bond delivers the enthalpic gain that drives reactions, such as the Wittig, Mitsunobu, and Appel reaction, to completion. However, phosphine oxides are recognized as undesirable waste products and in the past decade several methods have emerged that address this issue by in situ regeneration of the phosphorus reagent. This Minireview outlines the two distinct strategies and underpinning research that led to these advances. The potential of the emerging field of phosphorus catalysis in chemistry is shown and new developments that may stimulate further research are described.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  organocatalysis; phosphorus; reduction; waste prevention

Mesh:

Substances:

Year:  2013        PMID: 24039197     DOI: 10.1002/cssc.201300368

Source DB:  PubMed          Journal:  ChemSusChem        ISSN: 1864-5631            Impact factor:   8.928


  12 in total

1.  Biphilic Organophosphorus Catalysis: Regioselective Reductive Transposition of Allylic Bromides via P(III)/P(V) Redox Cycling.

Authors:  Kyle D Reichl; Nicole L Dunn; Nicholas J Fastuca; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2015-04-21       Impact factor: 15.419

Review 2.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

3.  Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane.

Authors:  Joseph A Buonomo; Carter G Eiden; Courtney C Aldrich
Journal:  Chemistry       Date:  2017-09-18       Impact factor: 5.236

4.  A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via PIII/PV═O Redox Cycling.

Authors:  Trevor V Nykaza; Tyler S Harrison; Avipsa Ghosh; Rachel A Putnik; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

5.  Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.

Authors:  Jeffrey M Lipshultz; Gen Li; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2021-01-19       Impact factor: 15.419

Review 6.  Phosphorus-Based Catalysis.

Authors:  Changmin Xie; Andrew J Smaligo; Xian-Rong Song; Ohyun Kwon
Journal:  ACS Cent Sci       Date:  2021-03-16       Impact factor: 14.553

Review 7.  Catalytic Wittig and aza-Wittig reactions.

Authors:  Zhiqi Lao; Patrick H Toy
Journal:  Beilstein J Org Chem       Date:  2016-11-30       Impact factor: 2.883

8.  Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination.

Authors:  Kui Zhang; Lingchao Cai; Zhongyue Yang; K N Houk; Ohyun Kwon
Journal:  Chem Sci       Date:  2018-01-18       Impact factor: 9.825

9.  Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C-N and C-C Bond Formation.

Authors:  Morgan Lecomte; Jeffrey M Lipshultz; Shin-Ho Kim-Lee; Gen Li; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2019-07-30       Impact factor: 15.419

10.  An Improved PIII/PV═O-Catalyzed Reductive C-N Coupling of Nitroaromatics and Boronic Acids by Mechanistic Differentiation of Rate- and Product-Determining Steps.

Authors:  Gen Li; Trevor V Nykaza; Julian C Cooper; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2020-03-25       Impact factor: 15.419

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