Literature DB >> 25514612

Gold-catalyzed intermolecular nitrene transfer from 2H-azirines to ynamides: a direct approach to polysubstituted pyrroles.

Lei Zhu1, Yinghua Yu, Zhifeng Mao, Xueliang Huang.   

Abstract

An effective gold-catalyzed intermolecular nitrene transfer by the reaction of 2H-azirines and ynamides is reported, which provides highly substituted pyrroles in a straightforward manner. This transformation proceeds under mild conditions and gives the polysubstituted pyrroles in good-to-excellent yields. Preliminary results indicate that a nongold carbenoid pathway is preferred for current pyrrole synthesis.

Entities:  

Year:  2014        PMID: 25514612     DOI: 10.1021/ol503172h

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


  12 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.  Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles.

Authors:  Yujing Zhou; Lin Zhou; Luke T Jesikiewicz; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

4.  Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines.

Authors:  Franz-Lucas Haut; Niklas J Feichtinger; Immanuel Plangger; Lukas A Wein; Mira Müller; Tim-Niclas Streit; Klaus Wurst; Maren Podewitz; Thomas Magauer
Journal:  J Am Chem Soc       Date:  2021-06-09       Impact factor: 15.419

5.  Synthesis of poly-functionalized benzofurans via one-pot domino oxidation/[3+2] cyclization reactions of a hydroquinone ester and ynamides.

Authors:  Dongxin Zhang; Jingjing Man; Yan Chen; Lei Yin; Junchao Zhong; Qian-Feng Zhang
Journal:  RSC Adv       Date:  2019-04-25       Impact factor: 4.036

6.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

7.  Divergent C-H Insertion-Cyclization Cascades of N-Allyl Ynamides.

Authors:  Holly V Adcock; Elli Chatzopoulou; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-30       Impact factor: 15.336

8.  Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.

Authors:  Manjeet K Majhail; Paul M Ylioja; Michael C Willis
Journal:  Chemistry       Date:  2016-04-23       Impact factor: 5.236

9.  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

10.  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

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