Literature DB >> 25839912

Fluoroalkylative aryl migration of conjugated N-arylsulfonylated amides using easily accessible sodium di- and monofluoroalkanesulfinates.

Zhengbiao He1, Ping Tan1, Chuanfa Ni1, Jinbo Hu1.   

Abstract

Fluorinated sulfinate salts RfSO2Na (Rf = CF2H, CF2Ph, and CH2F) have been prepared via NaBH4-mediated reduction of the corresponding benzo[d]thiazol-2-yl sulfones, and their synthetic application as di- and monofluoroalkyl radical precursors is demonstrated in the silver-catalyzed cascade fluoroalkylation/aryl migration/SO2 extrusion of conjugated N-arylsulfonylated amides.

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Year:  2015        PMID: 25839912     DOI: 10.1021/acs.orglett.5b00308

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


  10 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.  Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks.

Authors:  Wei Wei; Rama Kanwar Khangarot; Lothar Stahl; Cristina Veresmortean; Padmanava Pradhan; Lijia Yang; Barbara Zajc
Journal:  Org Lett       Date:  2018-06-01       Impact factor: 6.005

3.  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

Review 4.  Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds.

Authors:  Raju Jannapu Reddy; Arram Haritha Kumari
Journal:  RSC Adv       Date:  2021-03-01       Impact factor: 3.361

Review 5.  Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.

Authors:  Anthony R Allen; Efrey A Noten; Corey R J Stephenson
Journal:  Chem Rev       Date:  2021-10-21       Impact factor: 72.087

6.  A convenient approach to difluoromethylated all-carbon quaternary centers via Ni(ii)-catalyzed enantioselective Michael addition.

Authors:  Xuan Yu; Hui Bai; Dong Wang; Zhaohai Qin; Jia-Qi Li; Bin Fu
Journal:  RSC Adv       Date:  2018-05-25       Impact factor: 3.361

7.  Direct C-H difluoromethylation of heterocycles via organic photoredox catalysis.

Authors:  Wei Zhang; Xin-Xin Xiang; Junyi Chen; Chen Yang; Yu-Liang Pan; Jin-Pei Cheng; Qingbin Meng; Xin Li
Journal:  Nat Commun       Date:  2020-01-31       Impact factor: 14.919

8.  Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis.

Authors:  Sadayuki Arimori; Okiya Matsubara; Masahiro Takada; Motoo Shiro; Norio Shibata
Journal:  R Soc Open Sci       Date:  2016-05-25       Impact factor: 2.963

9.  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

10.  Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation-Defluorination Pathway.

Authors:  Zhiyao Zheng; Angela van der Werf; Marie Deliaval; Nicklas Selander
Journal:  Org Lett       Date:  2020-03-25       Impact factor: 6.005

  10 in total

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