Literature DB >> 19368376

N-Tosyl-S-difluoromethyl-S-phenylsulfoximine: a new difluoromethylation reagent for S-, N-, and C-nucleophiles.

Wei Zhang1, Fei Wang, Jinbo Hu.   

Abstract

The first alpha-difluoromethyl sulfoximine compound, 2, was successfully prepared by using the copper(II)-catalyzed nitrene transfer reaction. Compound 2 was found to be a novel and efficient difluoromethylation reagent for transferring the CF(2)H group to S-, N-, and C-nucleophiles. Deuterium-labeling experiments suggest that a difluorocarbene mechanism is involved in the current difluoromethylation reactions.

Entities:  

Year:  2009        PMID: 19368376     DOI: 10.1021/ol900567c

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


  14 in total

1.  Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.

Authors:  Conor E Brigham; Christian A Malapit; Naish Lalloo; Melanie S Sanford
Journal:  ACS Catal       Date:  2020-07-17       Impact factor: 13.084

2.  Conversion of Methyl Ketones and Methyl Sulfones into α-Deutero-α,α-Difluoromethyl Ketones and α-Deutero-α,α-Difluoromethyl Sulfones in Three Synthetic Steps.

Authors:  Munia F Sowaileh; Changho Han; Robert A Hazlitt; Eun Hoo Kim; Jinu P John; David A Colby
Journal:  Tetrahedron Lett       Date:  2016-12-21       Impact factor: 2.415

Review 3.  Synthesis and Transformations of NH-Sulfoximines.

Authors:  Michael Andresini; Arianna Tota; Leonardo Degennaro; James A Bull; Renzo Luisi
Journal:  Chemistry       Date:  2021-10-13       Impact factor: 5.020

4.  Stereospecific α-(hetero)arylation of sulfoximines and sulfonimidamides.

Authors:  Zachary P Shultz; Thomas Scattolin; Lukasz Wojtas; Justin M Lopchuk
Journal:  Nat Synth       Date:  2022-01-31

5.  Synthesis of Fluoroolefins via Julia-Kocienski Olefination.

Authors:  Barbara Zajc; Rakesh Kumar
Journal:  Synthesis (Stuttg)       Date:  2010       Impact factor: 3.157

6.  Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis.

Authors:  Marcus Frings; Isabelle Thomé; Carsten Bolm
Journal:  Beilstein J Org Chem       Date:  2012-09-03       Impact factor: 2.883

7.  Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine.

Authors:  Fei Wang; Lingchun Li; Chuanfa Ni; Jinbo Hu
Journal:  Beilstein J Org Chem       Date:  2014-02-06       Impact factor: 2.883

8.  Efficient Difluoromethylation of sp(3) Carbon Nucleophiles by Bromodifluoromethylation Reagents with Organic Bases.

Authors:  Guokai Liu; Xin Wang; Xu Lu; Xiu-Hua Xu; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2012-10-11       Impact factor: 2.911

9.  Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis.

Authors:  Sadayuki Arimori; Okiya Matsubara; Masahiro Takada; Motoo Shiro; Norio Shibata
Journal:  R Soc Open Sci       Date:  2016-05-25       Impact factor: 2.963

10.  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

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