Literature DB >> 33727978

Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes.

Xiaojuan Li1, Qiang Zhang1, Weigang Zhang1, Jinzhu Ma2, Yi Wang1, Yi Pan1.   

Abstract

The difunctionalization of alkenes involving a trifluoromethylthio group (SCF3) for the conversion of versatile and readily available olefins into structurally more complex molecules has been successfully studied. However, the disproportionate dithiolation of alkenes is unknown. Herein, a transition-metal-free protocol is presented for the vicinal trifluoromethylthio-thiolation of unactivated alkenes via a radical process under mild conditions with a broad substrate scope and excellent tolerance.
Copyright © 2021, Li et al.

Entities:  

Keywords:  alkenes; difunctionalization; metal-free; photoredox; trifluoromethylthiolation

Year:  2021        PMID： 33727978      PMCID： PMC7934782          DOI： 10.3762/bjoc.17.49

Source DB:  PubMed          Journal:  Beilstein J Org Chem        ISSN： 1860-5397            Impact factor:   2.883


  42 in total

1.  Chiral Selenide-Catalyzed Enantioselective Construction of Saturated Trifluoromethylthiolated Azaheterocycles.

Authors:  Jie Luo; Yannan Liu; Xiaodan Zhao
Journal:  Org Lett       Date:  2017-06-20       Impact factor: 6.005

2.  Synergistic Catalysis for the Umpolung Trifluoromethylthiolation of Tertiary Ethers.

Authors:  Wentao Xu; Junyang Ma; Xiang-Ai Yuan; Jie Dai; Jin Xie; Chengjian Zhu
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-12       Impact factor: 15.336

3.  Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes.

Authors:  Lvqi Jiang; Tianqi Ding; Wen-Bin Yi; Xin Zeng; Wei Zhang
Journal:  Org Lett       Date:  2018-04-06       Impact factor: 6.005

4.  Practical Photocatalytic Trifluoromethylation and Hydrotrifluoromethylation of Styrenes in Batch and Flow.

Authors:  Natan J W Straathof; Sten E Cramer; Volker Hessel; Timothy Noël
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-15       Impact factor: 15.336

5.  An N-(acetoxy)phthalimide motif as a visible-light pro-photosensitizer in photoredox decarboxylative arylthiation.

Authors:  Yunhe Jin; Haijun Yang; Hua Fu
Journal:  Chem Commun (Camb)       Date:  2016-10-25       Impact factor: 6.222

6.  Direct catalytic trifluoromethylthiolation of boronic acids and alkynes employing electrophilic shelf-stable N-(trifluoromethylthio)phthalimide.

Authors:  Roman Pluta; Pavlo Nikolaienko; Magnus Rueping
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-21       Impact factor: 15.336

7.  "Aromatic" substituent constants for structure-activity correlations.

Authors:  C Hansch; A Leo; S H Unger; K H Kim; D Nikaitani; E J Lien
Journal:  J Med Chem       Date:  1973-11       Impact factor: 7.446

8.  Direct trifluoromethylthiolation of unactivated C(sp(3))-H using silver(I) trifluoromethanethiolate and potassium persulfate.

Authors:  Hao Wu; Zhiwei Xiao; Junhui Wu; Yong Guo; Ji-Chang Xiao; Chao Liu; Qing-Yun Chen
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-23       Impact factor: 15.336

Review 9.  Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors:  Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal:  Chem Rev       Date:  2013-12-03       Impact factor: 60.622

10.  Visible-Light-Promoted Trifluoromethylthiolation of Styrenes by Dual Photoredox/Halide Catalysis.

Authors:  Roman Honeker; R Aleyda Garza-Sanchez; Matthew N Hopkinson; Frank Glorius
Journal:  Chemistry       Date:  2016-02-16       Impact factor: 5.236
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  1 in total

Review 1.  Recent advances in intermolecular 1,2-difunctionalization of alkenes involving trifluoromethylthiolation.

Authors:  Li Yan-Mei; Fu Jin-Feng; He Long-Qiang; Li Wei-Na; Esmail Vessally
Journal:  RSC Adv       Date:  2021-07-13       Impact factor: 4.036
  1 in total

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