Literature DB >> 14505394

The first general palladium catalyst for the Suzuki-Miyaura and carbonyl enolate coupling of aryl arenesulfonates.

Hanh Nho Nguyen1, Xiaohua Huang, Stephen L Buchwald.   

Abstract

The first general method for the palladium-catalyzed Suzuki-Miyaura and carbonyl enolate coupling of unactivated aryl arenesulfonates was developed utilizing XPhos, 1, and Pd(OAc)2. This is of significant interest because aryl tosylates and aryl benzenesulfonates are more easily handled and considerably less expensive than aryl triflates. This catalyst system effects the coupling of a variety of aryl, heteroaryl, and extremely hindered arylboronic acids with different aryl tosylates, under mild conditions. The same catalyst was employed in the first carbonyl enolate coupling of aryl arensulfonates.

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Year:  2003        PMID: 14505394     DOI: 10.1021/ja036947t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  28 in total

1.  Cross-Coupling Reactions of Alkenylsilanols with Fluoroalkylsulfonates: Development and Optimization of a Mild and Stereospecific Coupling Process.

Authors:  Scott E Denmark; Christopher S Regens
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  A novel 1,2-migration of acyloxy, phosphatyloxy, and sulfonyloxy groups in allenes: efficient synthesis of tri- and tetrasubstituted furans.

Authors:  Anna W Sromek; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-19       Impact factor: 15.336

Review 3.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors:  Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal:  Chem Rev       Date:  2010-12-06       Impact factor: 60.622

4.  Distinguishing between pathways for transmetalation in Suzuki-Miyaura reactions.

Authors:  Brad P Carrow; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-01-31       Impact factor: 15.419

5.  Selective monoarylation of acetate esters and aryl methyl ketones using aryl chlorides.

Authors:  Mark R Biscoe; Stephen L Buchwald
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

6.  Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature.

Authors:  Tokutaro Ogata; John F Hartwig
Journal:  J Am Chem Soc       Date:  2008-09-24       Impact factor: 15.419

Review 7.  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

8.  Suzuki-Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium complex catalyst.

Authors:  Guangming Nan; Fang Ren; Meiming Luo
Journal:  Beilstein J Org Chem       Date:  2010-06-28       Impact factor: 2.883

9.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

10.  Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles.

Authors:  Ryan A Altman; Alan M Hyde; Xiaohua Huang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2008-06-28       Impact factor: 15.419

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