Literature DB >> 23526683

Breaking the ring through a room temperature catalytic Wittig reaction.

Christopher J O'Brien1, Florie Lavigne, Emma E Coyle, Andrew J Holohan, Bryan J Doonan.   

Abstract

One ring no longer rules them all: Employment of 2.5-10 mol % of 4-nitrobenzoic acid with phenylsilane led to the development of a room temperature catalytic Wittig reaction (see scheme). Moreover, these enhanced reduction conditions also facilitated the use of acyclic phosphine oxides as catalysts for the first time. A series of alkenes were produced in moderate to high yield and selectivity.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2013        PMID: 23526683     DOI: 10.1002/chem.201300546

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  22 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.  Catalytic Asymmetric Staudinger-aza-Wittig Reaction for the Synthesis of Heterocyclic Amines.

Authors:  Lingchao Cai; Kui Zhang; Shuming Chen; Romain J Lepage; K N Houk; Elizabeth H Krenske; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2019-06-07       Impact factor: 15.419

5.  P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.

Authors:  Gen Li; Ziyang Qin; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2020-09-11       Impact factor: 15.419

6.  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

7.  Organophosphorus-Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by PIII /PV =O Redox Cycling.

Authors:  Avipsa Ghosh; Morgan Lecomte; Shin-Ho Kim-Lee; Alexander T Radosevich
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-25       Impact factor: 15.336

8.  Catalytic, asymmetric difluorination of alkenes to generate difluoromethylated stereocenters.

Authors:  Steven M Banik; Jonathan William Medley; Eric N Jacobsen
Journal:  Science       Date:  2016-07-01       Impact factor: 47.728

9.  Biphilic Organophosphorus-Catalyzed Intramolecular Csp2-H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations.

Authors:  Trevor V Nykaza; Antonio Ramirez; Tyler S Harrison; Michael R Luzung; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2018-02-12       Impact factor: 15.419

10.  Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PIII/PV═O Catalysis.

Authors:  Trevor V Nykaza; Julian C Cooper; Gen Li; Nolwenn Mahieu; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2018-11-02       Impact factor: 15.419

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.