Literature DB >> 25136973

Photoredox-catalyzed tandem radical cyclization of N-arylacrylamides: general methods to construct fluorinated 3,3-disubstituted 2-oxindoles using fluoroalkylsulfonyl chlorides.

Xiao-Jun Tang1, Charles S Thomoson, William R Dolbier.   

Abstract

Fluorinated radicals were generated from RfSO2Cl by photoredox catalysis under mild conditions, where Rf = n-C4F9, CF3, CF2H, CH2F, CH2CF3, and CF2CO2Me. This method provided a general way to construct fluorinated 2-oxindoles from reaction with N-arylacrylamides via a proposed tandem radical cyclization process.

Entities:  

Year:  2014        PMID： 25136973     DOI： 10.1021/ol502163f

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


  11 in total

1.  Radical Chlorodifluoromethylation: Providing a Motif for (Hetero)arene Diversification.

Authors:  Rory C McAtee; Joel W Beatty; Christopher C McAtee; Corey R J Stephenson
Journal:  Org Lett       Date:  2018-06-01       Impact factor: 6.005

2.  Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.

Authors:  Zhichao Lu; Olivia Hennis; Joseph Gentry; Bo Xu; Gerald B Hammond
Journal:  Org Lett       Date:  2020-05-13       Impact factor: 6.005

3.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

4.  Catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes to versatile enantioenriched-fluoroalkyl amines.

Authors:  Jin-Shun Lin; Fu-Li Wang; Xiao-Yang Dong; Wei-Wei He; Yue Yuan; Su Chen; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2017-03-23       Impact factor: 14.919

Review 5.  Progress in Difluoroalkylation of Organic Substrates by Visible Light Photoredox Catalysis.

Authors:  Agostinho Lemos; Christian Lemaire; André Luxen
Journal:  Adv Synth Catal       Date:  2019-01-17       Impact factor: 5.837

Review 6.  Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes.

Authors:  Bo Fu; Jorge Escorihuela; Jianlin Han; Santos Fustero; Pablo Barrio; Mikiko Sodeoka; Shintaro Kawamura; Alexander Sorochinsky; Vadim A Soloshonok
Journal:  Molecules       Date:  2021-11-28       Impact factor: 4.411

7.  Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones.

Authors:  Ping Qian; Bingnan Du; Wei Jiao; Haibo Mei; Jianlin Han; Yi Pan
Journal:  Beilstein J Org Chem       Date:  2016-02-17       Impact factor: 2.883

8.  Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols.

Authors:  Yusuke Arai; Ren Tomita; Gaku Ando; Takashi Koike; Munetaka Akita
Journal:  Chemistry       Date:  2015-12-16       Impact factor: 5.236

9.  CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF3SO2Cl.

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

10.  A remote C-C bond cleavage-enabled skeletal reorganization: Access to medium-/large-sized cyclic alkenes.

Authors:  Lei Li; Zhong-Liang Li; Qiang-Shuai Gu; Na Wang; Xin-Yuan Liu
Journal:  Sci Adv       Date:  2017-11-03       Impact factor: 14.136
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