Literature DB >> 26503292

Polysubstituted 2-Aminopyrrole Synthesis via Gold-Catalyzed Intermolecular Nitrene Transfer from Vinyl Azide to Ynamide: Reaction Scope and Mechanistic Insights.

Yufeng Wu1, Lei Zhu2, Yinghua Yu2, Xuesong Luo3, Xueliang Huang2.   

Abstract

A gold-catalyzed intermolecular reaction of vinyl azides and ynamides is described. This process presents an efficient and mild approach to multisubstituted 2-aminopyrroles in good-to-excellent yields. Control experiments were carried out to distinguish the reactivity between vinyl azides and the corresponding 2H-azirines. A plausible reaction mechanism was also proposed according to previous reports and our preliminary mechanistic studies.

Entities:  

Year:  2015        PMID: 26503292     DOI: 10.1021/acs.joc.5b02057

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  8 in total

1.  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

2.  Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles.

Authors:  Raju Jannapu Reddy; Matthew P Ball-Jones; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-19       Impact factor: 15.336

3.  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

4.  Dichotomy of platinum(II) and gold(III) carbene intermediates switching from N- to O-selectivity.

Authors:  Hongming Jin; Wen-Yan Tong; Jing Zhang; Matthias Rudolph; Frank Rominger; Xu Shen; Shuanglin Qu; A Stephen K Hashmi
Journal:  Nat Commun       Date:  2022-03-30       Impact factor: 14.919

Review 5.  Triflamides and Triflimides: Synthesis and Applications.

Authors:  Mikhail Y Moskalik; Vera V Astakhova
Journal:  Molecules       Date:  2022-08-15       Impact factor: 4.927

6.  Direct synthesis of pentasubstituted pyrroles and hexasubstituted pyrrolines from propargyl sulfonylamides and allenamides.

Authors:  Changqing Ye; Yihang Jiao; Mong-Feng Chiou; Yajun Li; Hongli Bao
Journal:  Chem Sci       Date:  2021-06-08       Impact factor: 9.825

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.  Acyl Migration versus Epoxidation in Gold Catalysis: Facile, Switchable, and Atom-Economic Synthesis of Acylindoles and Quinoline Derivatives.

Authors:  Xianhai Tian; Lina Song; Kaveh Farshadfar; Matthias Rudolph; Frank Rominger; Thomas Oeser; Alireza Ariafard; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336

  8 in total

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