Literature DB >> 30085396

Silver-Promoted Oxidative Benzylic C-H Trifluoromethoxylation.

Haodong Yang1, Feng Wang1, Xiaohuan Jiang1, Yu Zhou2, Xiufang Xu2, Pingping Tang1.   

Abstract

A silver-promoted oxidative benzylic C-H trifluoromethoxylation has been reported for the first time. With trifluoromethyl arylsulfonate as the trifluoromethoxylation reagent, various arenes, having diverse functional groups, undergo trifluoromethoxylation of their benzylic C-H bonds to form trifluoromethyl ethers under mild reaction conditions. In addition, the trifluoromethoxylation and the fluorination of methyl groups of electron-rich arenes have been achieved to prepare α-fluorobenzyl trifluoromethyl ethers in one step.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H functionalization; fluorine; reaction mechanisms; silver; synthetic methods

Year:  2018        PMID: 30085396     DOI: 10.1002/anie.201807144

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


  4 in total

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Journal:  Nat Rev Chem       Date:  2022-05-17       Impact factor: 34.571

2.  Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes.

Authors:  Zhichao Lu; Tatsuya Kumon; Gerald B Hammond; Teruo Umemoto
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-17       Impact factor: 16.823

3.  Copper-catalysed benzylic C-H coupling with alcohols via radical relay enabled by redox buffering.

Authors:  Huayou Hu; Si-Jie Chen; Mukunda Mandal; Saied Md Pratik; Joshua A Buss; Shane W Krska; Christopher J Cramer; Shannon S Stahl
Journal:  Nat Catal       Date:  2020-02-24

4.  Late-stage trifluoromethylthiolation of benzylic C-H bonds.

Authors:  Wentao Xu; Wenliang Wang; Tao Liu; Jin Xie; Chengjian Zhu
Journal:  Nat Commun       Date:  2019-10-25       Impact factor: 14.919

  4 in total

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