Literature DB >> 32400165

Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.

Zhichao Lu1, Olivia Hennis1, Joseph Gentry2, Bo Xu3, Gerald B Hammond1.   

Abstract

The base-induced reaction of aryl diazonium salts with commercially available CF3SO2Na/CF2HSO2Na allows for the generation of the corresponding diazene radicals along with fluoromethyl radicals. The addition of fluoromethyl radicals to alkenes with subsequent diazene trapping provides the azofluoromethylation products in good to excellent yields. This metal-free method under mild reaction conditions has broad functional group compatibility and is applicable in the late-stage modification of various natural products and bioactive molecules.

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Year:  2020        PMID： 32400165      PMCID： PMC7328341          DOI： 10.1021/acs.orglett.0c01395

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


  57 in total

1.  Synthesis and biological evaluation of novel analogues of the pan class I phosphatidylinositol 3-kinase (PI3K) inhibitor 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474).

Authors:  Gordon W Rewcastle; Swarna A Gamage; Jack U Flanagan; Raphael Frederick; William A Denny; Bruce C Baguley; Philip Kestell; Ripudaman Singh; Jackie D Kendall; Elaine S Marshall; Claire L Lill; Woo-Jeong Lee; Sharada Kolekar; Christina M Buchanan; Stephen M F Jamieson; Peter R Shepherd
Journal:  J Med Chem       Date:  2011-09-27       Impact factor: 7.446

2.  Recent progress in direct introduction of fluorinated groups on alkenes and alkynes by means of C-H bond functionalization.

Authors:  Tatiana Besset; Thomas Poisson; Xavier Pannecoucke
Journal:  Chemistry       Date:  2014-10-27       Impact factor: 5.236

Review 3.  Carbon trifluoromethylation reactions of hydrocarbon derivatives and heteroarenes.

Authors:  Concepción Alonso; Eduardo Martínez de Marigorta; Gloria Rubiales; Francisco Palacios
Journal:  Chem Rev       Date:  2015-01-30       Impact factor: 60.622

4.  Copper-catalyzed intermolecular trifluoromethylarylation of alkenes: mutual activation of arylboronic acid and CF3+ reagent.

Authors:  Fei Wang; Dinghai Wang; Xin Mu; Pinhong Chen; Guosheng Liu
Journal:  J Am Chem Soc       Date:  2014-07-08       Impact factor: 15.419

5.  Metal-free radical thiolations mediated by very weak bases.

Authors:  Denis Koziakov; Michal Majek; Axel Jacobi von Wangelin
Journal:  Org Biomol Chem       Date:  2016-11-24       Impact factor: 3.876

6.  Enantioselective Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes via Radical Process.

Authors:  Fei Wang; Dinghai Wang; Xiaolong Wan; Lianqian Wu; Pinhong Chen; Guosheng Liu
Journal:  J Am Chem Soc       Date:  2016-11-21       Impact factor: 15.419

Review 7.  Applications of Fluorine in Medicinal Chemistry.

Authors:  Eric P Gillis; Kyle J Eastman; Matthew D Hill; David J Donnelly; Nicholas A Meanwell
Journal:  J Med Chem       Date:  2015-07-22       Impact factor: 7.446

Review 8.  Oxidative trifluoromethylation and trifluoromethylthiolation reactions using (trifluoromethyl)trimethylsilane as a nucleophilic CF3 source.

Authors:  Lingling Chu; Feng-Ling Qing
Journal:  Acc Chem Res       Date:  2014-04-28       Impact factor: 22.384

9.  Radical Fluoroalkylation of Isocyanides with Fluorinated Sulfones by Visible-Light Photoredox Catalysis.

Authors:  Jian Rong; Ling Deng; Ping Tan; Chuanfa Ni; Yucheng Gu; Jinbo Hu
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-21       Impact factor: 15.336

10.  Radical C-H functionalization of heteroarenes under electrochemical control.

Authors:  Alexander G O'Brien; Akinobu Maruyama; Yasuhide Inokuma; Makoto Fujita; Phil S Baran; Donna G Blackmond
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-10       Impact factor: 15.336
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