Literature DB >> 11871908

Facile synthesis of N-aryl pyrroles via Cu(II)-mediated cross coupling of electron deficient pyrroles and arylboronic acids.

Shu Yu1, James Saenz, Jayaram K Srirangam.   

Abstract

N-Arylation of electron-deficient pyrroles has been achieved by cross-coupling with arylboronic acids at room temperature in the presence of stoichiometric amounts of copper(II) acetate. The generality of this reaction has been established with variously substituted pyrroles as well as boronic acids. A key intermediate in the synthesis of a matrix metalloprotease inhibitor has been achieved using this methodology.

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Year:  2002        PMID: 11871908     DOI: 10.1021/jo016131f

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


  7 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives.

Authors:  Gary A Molander; Sarah L J Trice; Spencer D Dreher
Journal:  J Am Chem Soc       Date:  2010-11-24       Impact factor: 15.419

3.  Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy; Spencer D Dreher; Matthew T Tudge
Journal:  J Am Chem Soc       Date:  2012-07-06       Impact factor: 15.419

4.  Continuous flow based catch and release protocol for the synthesis of alpha-ketoesters.

Authors:  Alessandro Palmieri; Steven V Ley; Anastasios Polyzos; Mark Ladlow; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2009-05-20       Impact factor: 2.883

5.  Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

Authors:  Gary A Molander; Livia N Cavalcanti; Carolina García-García
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

6.  Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds.

Authors:  Carolin Fischer; Burkhard Koenig
Journal:  Beilstein J Org Chem       Date:  2011-01-14       Impact factor: 2.883

7.  Prediction on the inhibition ratio of pyrrolidine derivatives on matrix metalloproteinase based on gene expression programming.

Authors:  Yuqin Li; Guirong You; Baoxiu Jia; Hongzong Si; Xiaojun Yao
Journal:  Biomed Res Int       Date:  2014-05-22       Impact factor: 3.411

  7 in total

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