Literature DB >> 26030605

Synthesis of Multiple-Substituted Pyrroles via Gold(I)-Catalyzed Hydroamination/Cyclization Cascade.

Xiangdong Li1, Ming Chen1, Xin Xie1, Ning Sun1, Shi Li1, Yuanhong Liu1.   

Abstract

A gold-catalyzed cascade hydroamination/cyclization reaction of α-amino ketones with alkynes to form substituted pyrroles has been developed. The method offers several advantages such as high regioselectivity with the tested cases, wide functional group tolerance, and easily accessible starting materials. The synthetic utility of the obtained pyrrole products was demonstrated by their efficient transformations to 2-vinylated pyrroles via gold-catalyzed intermolecular hydroarylation.

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Year:  2015        PMID： 26030605     DOI： 10.1021/acs.orglett.5b01281

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


  5 in total

1.  Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities.

Authors:  John T Gupton; Scott Yeudall; Nakul Telang; Megan Hoerrner; Ellis Huff; Evan Crawford; Katie Lounsbury; Michael Kimmel; William Curry; Andrew Harrison; Wen Juekun; Alex Shimozono; Joe Ortolani; Kristin Lescalleet; Jon Patteson; Veronica Moore-Stoll; Cristina C Rohena; Susan L Mooberry; Ahmad J Obaidullah; Glen E Kellogg; James A Sikorski
Journal:  Bioorg Med Chem       Date:  2017-04-11       Impact factor: 3.641

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

3.  Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles.

Authors:  John T Gupton; Alex Shimozono; Evan Crawford; Joe Ortolani; Evan Clark; Matt Mahoney; Campbell Heese; Jeffrey Noble; Carlos Perez Mandry; Rene Kanters; Raymond N Dominey; Emma W Goldman; James A Sikorski; Daniel C Fisher
Journal:  Tetrahedron       Date:  2018-04-07       Impact factor: 2.457

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.  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
  5 in total

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