Literature DB >> 26196678

Generation of α-Imino Gold Carbenes through Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides.

Chao Shu1, Yong-Heng Wang1, Bo Zhou1, Xin-Ling Li1, Yi-Fan Ping1, Xin Lu1, Long-Wu Ye1,2.   

Abstract

The generation of α-imino gold carbenes via gold-catalyzed intermolecular reaction of azides and ynamides is disclosed. This new methodology allows for highly regioselective access to valuable 2-aminoindoles and 3-amino-β-carbolines in generally good to excellent yields. A mechanistic rationale for this tandem reaction, especially for the observed high regioselectivity, is supported by DFT calculations.

Entities:  

Year:  2015        PMID: 26196678     DOI: 10.1021/jacs.5b06015

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  15 in total

1.  Investigations on Gold-Catalyzed Thioalkyne Activation Toward Facile Synthesis of Ketene Dithioacetals.

Authors:  Xiaohan Ye; Jin Wang; Shengtao Ding; Seyedmorteza Hosseyni; Lukasz Wojtas; Novruz G Akhmedov; Xiaodong Shi
Journal:  Chemistry       Date:  2017-07-20       Impact factor: 5.236

2.  Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers.

Authors:  Peter E Simm; Prakash Sekar; Jeffery Richardson; Paul W Davies
Journal:  ACS Catal       Date:  2021-05-13       Impact factor: 13.084

3.  Divergent synthesis of N-heterocycles via controllable cyclization of azido-diynes catalyzed by copper and gold.

Authors:  Wen-Bo Shen; Qing Sun; Long Li; Xin Liu; Bo Zhou; Juan-Zhu Yan; Xin Lu; Long-Wu Ye
Journal:  Nat Commun       Date:  2017-11-23       Impact factor: 14.919

4.  Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenes.

Authors:  Yuiki Kawada; Shunsuke Ohmura; Misaki Kobayashi; Wataru Nojo; Masaki Kondo; Yuka Matsuda; Junpei Matsuoka; Shinsuke Inuki; Shinya Oishi; Chao Wang; Tatsuo Saito; Masanobu Uchiyama; Takanori Suzuki; Hiroaki Ohno
Journal:  Chem Sci       Date:  2018-09-10       Impact factor: 9.825

5.  Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.

Authors:  Bo Zhou; Ying-Qi Zhang; Kairui Zhang; Ming-Yang Yang; Yang-Bo Chen; You Li; Qian Peng; Shou-Fei Zhu; Qi-Lin Zhou; Long-Wu Ye
Journal:  Nat Commun       Date:  2019-07-19       Impact factor: 14.919

6.  Metal-free intermolecular formal cycloadditions enable an orthogonal access to nitrogen heterocycles.

Authors:  Lan-Gui Xie; Supaporn Niyomchon; Antonio J Mota; Leticia González; Nuno Maulide
Journal:  Nat Commun       Date:  2016-03-15       Impact factor: 14.919

7.  Divergent ynamide reactivity in the presence of azides - an experimental and computational study.

Authors:  Veronica Tona; Stefan A Ruider; Martin Berger; Saad Shaaban; Mohan Padmanaban; Lan-Gui Xie; Leticia González; Nuno Maulide
Journal:  Chem Sci       Date:  2016-06-10       Impact factor: 9.825

8.  Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups.

Authors:  Bhanudas Dattatray Mokar; Prakash D Jadhav; Y B Pandit; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-04-23       Impact factor: 9.825

9.  Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C-H Aminations.

Authors:  Xianhai Tian; Lina Song; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-02       Impact factor: 15.336

10.  Synthesis of 3-Amino-1-benzothiophene-1,1-diones by Alkyne Directed Hydroarylation and 1/N→3/C-Sulfonyl Migration.

Authors:  Ivan Bernar; Daniel Blanco-Ania; Sophie J Stok; Lia Sotorríos; Enrique Gómez-Bengoa; Floris P J T Rutjes
Journal:  European J Org Chem       Date:  2018-10-10
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