Literature DB >> 26649920

NMP and O2 as Radical Initiator: Trifluoromethylation of Alkenes to Tertiary β-Trifluoromethyl Alcohols at Room Temperature.

Chao Liu1, Qingquan Lu1, Zhiyuan Huang1, Jian Zhang1, Fan Liao2, Pan Peng1, Aiwen Lei1,3.   

Abstract

A novel strategy was developed to trigger ·CF3 by using in situ generated peroxide in NMP under O2 or air as the radical initiator. Radical trifluoromethylation of alkenes was achieved toward tertiary β-trifluoromethyl alcohols. Various tertiary β-trifluoromethyl alcohols can be synthesized in good yields without extra oxidants or transition metal catalysts. Preliminary mechanistic investigation revealed that O2 diffusion can influence the reaction rate.

Entities:  

Year:  2015        PMID: 26649920     DOI: 10.1021/acs.orglett.5b03035

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


  5 in total

1.  Copper(i) reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one.

Authors:  Qing Wang; Peng Shi; Runsheng Zeng
Journal:  RSC Adv       Date:  2018-07-19       Impact factor: 4.036

Review 2.  Radicals: Reactive Intermediates with Translational Potential.

Authors:  Ming Yan; Julian C Lo; Jacob T Edwards; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

3.  CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na.

Authors:  Hélène Guyon; Hélène Chachignon; Dominique Cahard
Journal:  Beilstein J Org Chem       Date:  2017-12-19       Impact factor: 2.883

4.  Metal-free alkene oxy- and amino-perfluoroalkylations via carbocation formation by using perfluoro acid anhydrides: unique reactivity between styrenes and perfluoro diacyl peroxides.

Authors:  Elena Valverde; Shintaro Kawamura; Daisuke Sekine; Mikiko Sodeoka
Journal:  Chem Sci       Date:  2018-08-01       Impact factor: 9.825

5.  Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water.

Authors:  Sadhan Jana; Ajay Verma; Rahul Kadu; Sangit Kumar
Journal:  Chem Sci       Date:  2017-07-10       Impact factor: 9.825

  5 in total

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