Literature DB >> 30534708

Ruthenium-catalyzed synthesis of indole derivatives from N-aryl-2-aminopyridines and alpha-carbonyl sulfoxonium ylides.

Xin-Feng Cui1, Zi-Hui Ban, Wa-Fa Tian, Fang-Peng Hu, Xiao-Qiang Zhou, Hao-Jie Ma, Zhen-Zhen Zhan, Guo-Sheng Huang.   

Abstract

Indole is a ubiquitous structural motif with important applications in many areas of chemistry. Given this, a simple and efficient Ru(ii)-catalyzed synthesis of indole via intermolecular annulation of N-aryl-2-aminopyridines and sulfoxonium ylides was proposed and accomplished. Excellent selectivity and good functional group tolerance of this transformation were observed. This protocol provides easy access to a wide variety of useful indoles in the presence of a commercially available [Ru(p-cymene)Cl2]2 catalyst. A possible mechanism for the reaction pathway was also proposed. More importantly, this reaction will offer a useful method for the construction of enantioenriched indole frameworks.

Entities:  

Year:  2019        PMID: 30534708     DOI: 10.1039/c8ob02818d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  4 in total

Review 1.  Asymmetric transformations from sulfoxonium ylides.

Authors:  Clarice A D Caiuby; Lucas G Furniel; Antonio C B Burtoloso
Journal:  Chem Sci       Date:  2021-12-08       Impact factor: 9.825

2.  Rhodium(iii)-catalyzed C-H annulation of 2-acetyl-1-arylhydrazines with sulfoxonium ylides: synthesis of 2-arylindoles.

Authors:  He Li; Ye Lu; Xinxin Jin; Shuang Sun; Limei Duan; Jinghai Liu
Journal:  RSC Adv       Date:  2020-10-30       Impact factor: 4.036

3.  Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls.

Authors:  Daniel Clare; Benjamin C Dobson; Phillip A Inglesby; Christophe Aïssa
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-24       Impact factor: 15.336

4.  Ruthenium(II)-Catalyzed Homocoupling of α-Carbonyl Sulfoxonium Ylides Under Mild Conditions: Methodology Development and Mechanistic DFT Study.

Authors:  Maosheng Zhang; Jinrong Zhang; Zhenfang Teng; Jianhui Chen; Yuanzhi Xia
Journal:  Front Chem       Date:  2020-09-16       Impact factor: 5.221

  4 in total

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