Literature DB >> 24339161

PhI(OAc)(2) -mediated radical trifluoromethylation of vinyl azides with Me(3)SiCF(3).

Yi-Feng Wang1, Geoffroy Hervé Lonca, Shunsuke Chiba.   

Abstract

The fluorine-containing organic motif is becoming privileged in pharmaceuticals, agrochemicals, and functional materials, owing to its unique properties such as electron-withdrawing character, metabolic stability, and lipophilicity. Described herein is the PhI(OAc)2 -mediated radical trifluoromethylation of vinyl azides with Me3 SiCF3 to efficiently generate α-trifluoromethyl azines. The resulting α-trifluoromethyl azines were successfully transformed to valuable fluorine-containing molecules such as α-trifluoromethyl ketones, β-trifluoromethyl amines, 5-fluoropyrazoles, and trifluoroethyl isoquinolines.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  fluorine; heterocycles; hypervalent iodine; radicals; synthetic methods

Mesh:

Substances:

Year:  2013        PMID: 24339161     DOI: 10.1002/anie.201307846

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


  5 in total

Review 1.  Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis.

Authors:  Bao Hu; Stephen G DiMagno
Journal:  Org Biomol Chem       Date:  2015-04-07       Impact factor: 3.876

2.  Photoinduced Trifluoromethylation with CF3Br as a Trifluoromethyl Source: Synthesis of α-CF3-Substituted Ketones.

Authors:  Ransong Ma; Zhoubin Deng; Ke-Hu Wang; Junjiao Wang; Danfeng Huang; Yingpeng Su; Yulai Hu; Xiaobo Lv
Journal:  ACS Omega       Date:  2022-04-12

Review 3.  Addition of CF3 across unsaturated moieties: a powerful functionalization tool.

Authors:  Estíbaliz Merino; Cristina Nevado
Journal:  Chem Soc Rev       Date:  2014-05-02       Impact factor: 54.564

4.  Direct Synthesis of Symmetrical Azines from Alcohols and Hydrazine Catalyzed by a Ruthenium Pincer Complex: Effect of Hydrogen Bonding.

Authors:  Jonathan O Bauer; Gregory Leitus; Yehoshoa Ben-David; David Milstein
Journal:  ACS Catal       Date:  2016-11-17       Impact factor: 13.084

5.  Kinetic resolution of cyclic benzylic azides enabled by site- and enantioselective C(sp3)-H oxidation.

Authors:  Pengbo Ye; Aili Feng; Lin Wang; Min Cao; Rongxiu Zhu; Lei Liu
Journal:  Nat Commun       Date:  2022-03-25       Impact factor: 14.919

  5 in total

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