Literature DB >> 25423177

Difluoromethylene phosphabetaine as an equivalent of difluoromethyl carbanion.

Vitalij V Levin1, Alexey L Trifonov, Artem A Zemtsov, Marina I Struchkova, Dmitry E Arkhipov, Alexander D Dilman.   

Abstract

A method for nucleophilic difluoromethylation of reactive Michael acceptors, aldehydes, and azomethines is described. The reaction is performed using the readily available and air-stable reagent difluoromethylene phosphabetaine. The process involves interaction of an electrophilic substrate with in situ generated difluorinated phosphonium ylide followed by hydrolysis of the carbon-phosphorus bond under mild conditions.

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Year:  2014        PMID: 25423177     DOI: 10.1021/ol503225s

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  An Unconventional Mechanistic Insight into SCF3 Formation from Difluorocarbene: Preparation of 18 F-Labeled α-SCF3 Carbonyl Compounds.

Authors:  Jian Zheng; Ran Cheng; Jin-Hong Lin; Dong-Hai Yu; Longle Ma; Lina Jia; Lan Zhang; Lu Wang; Ji-Chang Xiao; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-14       Impact factor: 15.336

2.  Overcoming Kinetic and Thermodynamic Challenges of Classic Cope Rearrangements.

Authors:  Ehsan Fereyduni; Ouidad Lahtigui; Jacob N Sanders; Breanna M Tomiczek; Michael D Mannchen; Roland A Yu; K N Houk; Alexander J Grenning
Journal:  J Org Chem       Date:  2021-01-21       Impact factor: 4.354

3.  Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

Authors:  Jian Zheng; Lu Wang; Jin-Hong Lin; Ji-Chang Xiao; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-21       Impact factor: 15.336

Review 4.  Photocatalytic Difluoromethylation Reactions of Aromatic Compounds and Aliphatic Multiple C-C Bonds.

Authors:  Sebastián Barata-Vallejo; Al Postigo
Journal:  Molecules       Date:  2019-12-06       Impact factor: 4.411

5.  Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols.

Authors:  Yusuke Arai; Ren Tomita; Gaku Ando; Takashi Koike; Munetaka Akita
Journal:  Chemistry       Date:  2015-12-16       Impact factor: 5.236

  5 in total

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