Literature DB >> 16388664

Modified palladium-catalyzed Sonogashira cross-coupling reactions under copper-, amine-, and solvent-free conditions.

Yun Liang1, Ye-Xiang Xie, Jin-Heng Li.   

Abstract

[reaction: see text] PdCl2(PPh3)2 combined with TBAF under solvent-free conditions provided general and fast Sonogashira cross-coupling reactions of aryl halides with terminal alkynes. In particular, this protocol could be applied to the reactions of deactivated aryl chlorides. In the presence of 3 mol % of PdCl2(PPh3)2 and 3 equiv of TBAF, a number of ArX species (X = I, Br, Cl) were coupled with alkynes to afford the corresponding products in moderate to excellent yields under copper-, amine-, and solvent-free conditions.

Entities:  

Year:  2006        PMID: 16388664     DOI: 10.1021/jo051882t

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


  9 in total

1.  Efficient Pd-catalyzed coupling of tautomerizable heterocycles with terminal alkynes via C-OH bond activation using PyBrOP.

Authors:  Ce Shi; Courtney C Aldrich
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

2.  High-fidelity hydrophilic probe for two-photon fluorescence lysosomal imaging.

Authors:  Xuhua Wang; Dao M Nguyen; Ciceron O Yanez; Luis Rodriguez; Hyo-Yang Ahn; Mykhailo V Bondar; Kevin D Belfield
Journal:  J Am Chem Soc       Date:  2010-09-08       Impact factor: 15.419

3.  Novel Cinchona alkaloid derived ammonium salts as catalysts for the asymmetric synthesis of beta-hydroxy alpha-amino acids via aldol reactions.

Authors:  Bing Ma; Jared L Parkinson; Steven L Castle
Journal:  Tetrahedron Lett       Date:  2007-03-19       Impact factor: 2.415

4.  Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions.

Authors:  Deyun Qian; Junliang Zhang
Journal:  Beilstein J Org Chem       Date:  2011-06-15       Impact factor: 2.883

5.  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

6.  Design, synthesis and evaluation of novel 2,2-dimethyl-2,3-dihydroquinolin-4(1H)-one based chalcones as cytotoxic agents.

Authors:  Julie Jean; David S Farrell; Angela M Farrelly; Sinead Toomey; James W Barlow
Journal:  Heliyon       Date:  2018-09-04

7.  Olefin-accelerated solid-state C-N cross-coupling reactions using mechanochemistry.

Authors:  Koji Kubota; Tamae Seo; Katsumasa Koide; Yasuchika Hasegawa; Hajime Ito
Journal:  Nat Commun       Date:  2019-01-10       Impact factor: 14.919

8.  Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry.

Authors:  Koji Kubota; Emiru Baba; Tamae Seo; Tatsuo Ishiyama; Hajime Ito
Journal:  Beilstein J Org Chem       Date:  2022-07-18       Impact factor: 2.544

Review 9.  Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

Authors:  Christopher S Horbaczewskyj; Ian J S Fairlamb
Journal:  Org Process Res Dev       Date:  2022-07-11       Impact factor: 3.858

  9 in total

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