Literature DB >> 33443440

Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates.

Zhi-Yun Liu1, Silas P Cook1.   

Abstract

The site-selective trifluoromethylation of aliphatic systems remains an important challenge. This work describes a light-driven, copper-mediated trifluoromethylation of O-alkyl thiocarbonates. The reaction provides broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), thereby offering orthogonality and practicality for trifluoromethylation. A radical organometallic mechanism is proposed.

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Year:  2021        PMID： 33443440      PMCID： PMC9558134          DOI： 10.1021/acs.orglett.0c04039

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.072


  85 in total

1.  Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides.

Authors:  Mengyu Gao; Deli Sun; Hegui Gong
Journal:  Org Lett       Date:  2019-02-25       Impact factor: 6.005

Review 2.  Trifluoromethylation of alkenes with concomitant introduction of additional functional groups.

Authors:  Hiromichi Egami; Mikiko Sodeoka
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-24       Impact factor: 15.336

Review 3.  Catalysis for fluorination and trifluoromethylation.

Authors:  Takeru Furuya; Adam S Kamlet; Tobias Ritter
Journal:  Nature       Date:  2011-05-26       Impact factor: 49.962

4.  1,6-Addition of Tertiary Carbon Radicals Generated From Alcohols or Carboxylic Acids by Visible-Light Photoredox Catalysis.

Authors:  Samir Y Abbas; Peng Zhao; Larry E Overman
Journal:  Org Lett       Date:  2018-01-23       Impact factor: 6.005

5.  Trifluoromethylation of Alkyl Radicals in Aqueous Solution.

Authors:  Haigen Shen; Zhonglin Liu; Pei Zhang; Xinqiang Tan; Zhenzhen Zhang; Chaozhong Li
Journal:  J Am Chem Soc       Date:  2017-07-12       Impact factor: 15.419

6.  Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides.

Authors:  Xiaheng Zhang; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2016-10-17       Impact factor: 15.419

7.  Copper-Mediated Trifluoromethylation of Benzylic Csp3 -H Bonds.

Authors:  Matthew Paeth; William Carson; Jheng-Hua Luo; David Tierney; Zhi Cao; Mu-Jeng Cheng; Wei Liu
Journal:  Chemistry       Date:  2018-07-18       Impact factor: 5.236

8.  Copper-Catalyzed Trifluoromethylation of Polysubstituted Alkenes Assisted by Decarboxylation.

Authors:  Zhengbiao He; Ping Tan; Jinbo Hu
Journal:  Org Lett       Date:  2015-12-14       Impact factor: 6.005

9.  Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling.

Authors:  Christopher C Nawrat; Christopher R Jamison; Yuriy Slutskyy; David W C MacMillan; Larry E Overman
Journal:  J Am Chem Soc       Date:  2015-08-31       Impact factor: 15.419

10.  Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates.

Authors:  Brett R Ambler; Lingui Zhu; Ryan A Altman
Journal:  J Org Chem       Date:  2015-08-11       Impact factor: 4.354
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