Literature DB >> 16468712

Development of a novel, highly efficient halide-catalyzed sulfenylation of indoles.

Matthew Tudge1, Minoru Tamiya, Cecile Savarin, Guy R Humphrey.   

Abstract

[reaction: see text] The reaction of a variety of indoles with N-thioalkyl- and N-thioarylphthalimides to produce 3-thioindoles is reported. Catalytic quantities of halide-containing salts are crucial to the success of this reaction. This highly efficient reaction provides sulfenylated indoles from bench-stable, readily available starting materials in good to excellent yields.

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Year:  2006        PMID： 16468712     DOI： 10.1021/ol052615c

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


  9 in total

1.  Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

Authors:  Yu Chen; Chul-Hee Cho; Feng Shi; Richard C Larock
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

2.  A novel synthetic route to 3-sulfenyl- and 3-selenylindoles by n-Bu4NI-induced electrophilic cyclization.

Authors:  Yu Chen; Chul-Hee Cho; Richard C Larock
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

3.  I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.

Authors:  Wei Fan; Zhen Yang; Bo Jiang; Guigen Li
Journal:  Org Chem Front       Date:  2017-02-20       Impact factor: 5.281

4.  Transition-metal-free synthesis of 3-sulfenylated chromones via KIO3-catalyzed radical C(sp2)-H sulfenylation.

Authors:  Yanhui Guo; Shanshan Zhong; Li Wei; Jie-Ping Wan
Journal:  Beilstein J Org Chem       Date:  2017-09-27       Impact factor: 2.883

5.  Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade.

Authors:  Mindaugas Šiaučiulis; Selma Sapmaz; Alexander P Pulis; David J Procter
Journal:  Chem Sci       Date:  2017-11-17       Impact factor: 9.825

6.  Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions.

Authors:  Qing Huang; Xiangjun Peng; Hong Li; Haiping He; Liangxian Liu
Journal:  Molecules       Date:  2022-01-25       Impact factor: 4.411

7.  Ultrasound-promoted two-step synthesis of 3-arylselenylindoles and 3-arylthioindoles as novel combretastatin A-4 analogues.

Authors:  Zhiyong Wen; Xiaona Li; Daiying Zuo; Binyue Lang; Yang Wu; Mingyang Jiang; Huizhuo Ma; Kai Bao; Yingliang Wu; Weige Zhang
Journal:  Sci Rep       Date:  2016-04-05       Impact factor: 4.379

8.  Copper-catalysed regioselective sulfenylation of indoles with sodium sulfinates.

Authors:  Xiaojun Luo; Qiang Liu; Hongxia Zhu; Huoji Chen
Journal:  R Soc Open Sci       Date:  2018-05-30       Impact factor: 2.963

9.  A selenium-based ionic liquid as a recyclable solvent for the catalyst-free synthesis of 3-selenylindoles.

Authors:  Everton G Zimmermann; Samuel Thurow; Camilo S Freitas; Samuel R Mendes; Gelson Perin; Diego Alves; Raquel G Jacob; Eder J Lenardão
Journal:  Molecules       Date:  2013-04-05       Impact factor: 4.411
  9 in total

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