Literature DB >> 23841459

General and regioselective synthesis of pyrroles via ruthenium-catalyzed multicomponent reactions.

Min Zhang1, Xianjie Fang, Helfried Neumann, Matthias Beller.   

Abstract

A general and highly regioselective synthesis of pyrroles via ruthenium-catalyzed three-component reactions has been developed. A variety of ketones including less reactive aryl and alkyl substrates were efficiently converted in combination with different type of amines and vicinal diols into various substituted pyrroles in reasonable to excellent isolated yields. Additionally, α-functionalized ketones gave synthetically interesting amido-, alkoxy-, aryloxy-, and phosphate-substituted pyrroles in a straightforward manner. The synthetic protocol proceeds in the presence of a commercially available ruthenium catalyst system and catalytic amount of base. It proceeds with high atom-efficiency and shows a broad substrate scope and functional group tolerance, making it a highly practical approach for preparation of various pyrrole derivatives.

Entities:  

Year:  2013        PMID: 23841459     DOI: 10.1021/ja406666r

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


  11 in total

1.  Ruthenium-Catalyzed Amination of Secondary Alcohols using Borrowing Hydrogen Methodology.

Authors:  Kostiantyn O Marichev; James M Takacs
Journal:  ACS Catal       Date:  2016-02-23       Impact factor: 13.084

2.  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

Review 3.  Synthesis of N-Heterocycles via Oxidant-Free Dehydrocyclization of Alcohols Using Heterogeneous Catalysts.

Authors:  Kangkang Sun; Hongbin Shan; Guo-Ping Lu; Chun Cai; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-03       Impact factor: 16.823

4.  Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles.

Authors:  Wei Wen Tan; Naohiko Yoshikai
Journal:  Chem Sci       Date:  2015-08-03       Impact factor: 9.825

5.  Hydrogen Transfer-Mediated Multicomponent Reaction for Direct Synthesis of Quinazolines by a Naphthyridine-Based Iridium Catalyst.

Authors:  Zhenda Tan; Zhongxin Fu; Jian Yang; Yang Wu; Liang Cao; Huanfeng Jiang; Juan Li; Min Zhang
Journal:  iScience       Date:  2020-03-21

6.  Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles.

Authors:  Wenbo Huang; Kaimei Wang; Ping Liu; Minghao Li; Shaoyong Ke; Yanlong Gu
Journal:  Beilstein J Org Chem       Date:  2020-11-30       Impact factor: 2.883

Review 7.  Sustainable catalysis with fluxional acridine-based PNP pincer complexes.

Authors:  Sayan Kar; David Milstein
Journal:  Chem Commun (Camb)       Date:  2022-03-18       Impact factor: 6.222

8.  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

9.  Catalytic condensation for the formation of polycyclic heteroaromatic compounds.

Authors:  Daniel Forberg; Tobias Schwob; Rhett Kempe
Journal:  Nat Commun       Date:  2018-05-01       Impact factor: 14.919

10.  Pseudo-four component synthesis of mono- and di-benzylated-1,2,3-triazoles derived from aniline.

Authors:  Daniel Mendoza-Espinosa; Guillermo E Negron-Silva; Leticia Lomas-Romero; Atilano Gutierrez-Carrillo; Rosa Santillán
Journal:  Molecules       Date:  2013-12-20       Impact factor: 4.411

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