Literature DB >> 24123914

N-trifluoromethylthiophthalimide: a stable electrophilic SCF3 -reagent and its application in the catalytic asymmetric trifluoromethylsulfenylation.

Teerawut Bootwicha1, Xiangqian Liu, Roman Pluta, Iuliana Atodiresei, Magnus Rueping.   

Abstract

Cinchona alkaloid catalysts in combination with air- and moisture-stable N-trifluoromethylthiophthalimide as electrophilic SCF3 source enabled the catalytic enantioselective trifluoromethylsulfenylation. Thus, a series of α-SCF3 esters that bear a quaternary carbon stereogenic center were obtained with excellent yield and enantioselectivity. Moreover, the products can be readily converted into valuable α-SCF3 β-hydroxyesters.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cinchona alkaloids; fluorine; indanones; organocatalysis; trifluoromethylsulfenylation

Year:  2013        PMID: 24123914     DOI: 10.1002/anie.201304957

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  12 in total

Review 1.  The Cation-π Interaction in Small-Molecule Catalysis.

Authors:  C Rose Kennedy; Song Lin; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-22       Impact factor: 15.336

2.  Structural reevaluation of the electrophilic hypervalent iodine reagent for trifluoromethylthiolation supported by the crystalline sponge method for X-ray analysis.

Authors:  Ekaterina V Vinogradova; Peter Müller; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

3.  Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers.

Authors:  Jian He; Caiyou Chen; Gregory C Fu; Jonas C Peters
Journal:  ACS Catal       Date:  2018-10-31       Impact factor: 13.084

4.  Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides.

Authors:  Zhikun Zhang; Zhe Sheng; Weizhi Yu; Guojiao Wu; Rui Zhang; Wen-Dao Chu; Yan Zhang; Jianbo Wang
Journal:  Nat Chem       Date:  2017-06-05       Impact factor: 24.427

5.  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

6.  N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity.

Authors:  Niranjan Thota; Parameshwar Makam; Kamal K Rajbongshi; Savania Nagiah; Naeem Sheik Abdul; Anil A Chuturgoon; Amit Kaushik; Gyanu Lamichhane; Anou M Somboro; Hendrik G Kruger; Thavendran Govender; Tricia Naicker; Per I Arvidsson
Journal:  ACS Med Chem Lett       Date:  2019-09-11       Impact factor: 4.345

7.  Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

Authors:  Yong Li; Zhishi Ye; Tabitha M Bellman; Teng Chi; Mingji Dai
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.072

Review 8.  Advances in catalytic enantioselective fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation reactions.

Authors:  Xiaoyu Yang; Tao Wu; Robert J Phipps; F Dean Toste
Journal:  Chem Rev       Date:  2014-10-22       Impact factor: 60.622

9.  2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions.

Authors:  Zhongyan Huang; Kenta Okuyama; Chen Wang; Etsuko Tokunaga; Xiaorui Li; Norio Shibata
Journal:  ChemistryOpen       Date:  2016-01-28       Impact factor: 2.911

10.  Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation.

Authors:  Jie Luo; Qingxiang Cao; Xiaohui Cao; Xiaodan Zhao
Journal:  Nat Commun       Date:  2018-02-06       Impact factor: 14.919

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