Literature DB >> 18683937

Sonogashira couplings of aryl bromides: room temperature, water only, no copper.

Bruce H Lipshutz1, David W Chung, Brian Rich.   

Abstract

Cross-coupling reactions between lipophilic terminal alkynes and aryl bromides can be catalyzed by ligated Pd, in the absence of copper, in pure water at ambient temperatures. Small amounts of the nonionic amphiphile PTS assist by virtue of nanometer micelles formed spontaneously in an aqueous medium.

Entities:  

Year:  2008        PMID： 18683937     DOI： 10.1021/ol801471f

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


  13 in total

1.  "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

2.  "Nok": a phytosterol-based amphiphile enabling transition-metal-catalyzed couplings in water at room temperature.

Authors:  Piyatida Klumphu; Bruce H Lipshutz
Journal:  J Org Chem       Date:  2014-01-21       Impact factor: 4.354

3.  Aminations of Aryl Bromides in Water at Room Temperature.

Authors:  Bruce H Lipshutz; David W Chung; Brian Rich
Journal:  Adv Synth Catal       Date:  2009-08       Impact factor: 5.837

4.  Manipulating micellar environments for enhancing transition metal-catalyzed cross-couplings in water at room temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai; Wendy Wen Yi Leong; Benjamin R Taft; Daniel V Krogstad
Journal:  J Org Chem       Date:  2011-05-19       Impact factor: 4.354

5.  TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai; Alexander R Abela; Ralph Moser; Takashi Nishikata; Christophe Duplais; Arkady Krasovskiy; Ricky D Gaston; Robert C Gadwood
Journal:  J Org Chem       Date:  2011-05-09       Impact factor: 4.354

Review 6.  Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives.

Authors:  Andrew Jordan; Callum G J Hall; Lee R Thorp; Helen F Sneddon
Journal:  Chem Rev       Date:  2022-02-24       Impact factor: 72.087

Review 7.  Organic synthesis "on water".

Authors:  Arani Chanda; Valery V Fokin
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622

8.  Synthesis and characterization of a heteroleptic Ru(II) complex of phenanthroline containing oligo-anthracenyl carboxylic acid moieties.

Authors:  Adewale O Adeloye; Peter A Ajibade
Journal:  Int J Mol Sci       Date:  2010-09-08       Impact factor: 5.923

9.  Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions.

Authors:  Andrea Caporale; Stefano Tartaggia; Andrea Castellin; Ottorino De Lucchi
Journal:  Beilstein J Org Chem       Date:  2014-02-12       Impact factor: 2.883

10.  Synthesis and characterization of a Ru(II) complex with functionalized phenanthroline ligands having single-double linked anthracenyl and 1-methoxy-1-buten-3-yne moieties.

Authors:  Adewale O Adeloye; Peter A Ajibade
Journal:  Molecules       Date:  2010-10-27       Impact factor: 4.411
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