Literature DB >> 17602563

Easily accessible and highly tunable indolyl phosphine ligands for Suzuki-Miyaura coupling of aryl chlorides.

Chau Ming So1, Chak Po Lau, Fuk Yee Kwong.   

Abstract

This study describes a new class of easily accessible indolyl phosphine ligands, prepared via an efficient protocol involving Fischer indolization from readily available phenylhydrazine and substituted acetophenones. This versatile ligand scaffold provides beneficial features, including high potential of steric and electronic tunability. The air-stable indolyl phosphines in combination with a palladium metal precursor provide highly effective catalysts for Suzuki-Miyaura coupling of unactivated aryl chlorides, and the catalyst loading down to 0.02 mol % can be achieved.

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Year:  2007        PMID: 17602563     DOI: 10.1021/ol070898y

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


  17 in total

1.  A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

Authors:  Bing Zheng; Tiezheng Jia; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-01-13       Impact factor: 5.837

Review 2.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

3.  Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.

Authors:  Bing Zheng; Minyan Li; Gui Gao; Yuying He; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2016-06-15       Impact factor: 5.837

4.  Palladium-Catalyzed Direct α-Aryation of Benzyl Thioethers with Aryl Bromides.

Authors:  Gustavo Frensch; Nusrah Hussain; Francisco A Marques; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-08-11       Impact factor: 5.837

Review 5.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides.

Authors:  Spencer D Dreher; Siang-Ee Lim; Deidre L Sandrock; Gary A Molander
Journal:  J Org Chem       Date:  2009-05-15       Impact factor: 4.354

7.  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands.

Authors:  Ruben Martin; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

8.  Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors.

Authors:  Giuseppe La Regina; Ruoli Bai; Whilelmina Maria Rensen; Erica Di Cesare; Antonio Coluccia; Francesco Piscitelli; Valeria Famiglini; Alessia Reggio; Marianna Nalli; Sveva Pelliccia; Eleonora Da Pozzo; Barbara Costa; Ilaria Granata; Amalia Porta; Bruno Maresca; Alessandra Soriani; Maria Luisa Iannitto; Angela Santoni; Junjie Li; Marlein Miranda Cona; Feng Chen; Yicheng Ni; Andrea Brancale; Giulio Dondio; Stefania Vultaggio; Mario Varasi; Ciro Mercurio; Claudia Martini; Ernest Hamel; Patrizia Lavia; Ettore Novellino; Romano Silvestri
Journal:  J Med Chem       Date:  2012-12-27       Impact factor: 7.446

9.  Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles.

Authors:  Chen Hu; Gang Hong; Yuchen He; Chen Zhou; Marisa C Kozlowski; Limin Wang
Journal:  J Org Chem       Date:  2018-04-04       Impact factor: 4.354

10.  Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal.

Authors:  Vardan Papoian; Thomas Minehan
Journal:  J Org Chem       Date:  2008-08-22       Impact factor: 4.354

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