Literature DB >> 20740063

An Efficient System For the Pd-Catalyzed Cross-Coupling of Amides and Aryl Chlorides.

Brett P Fors1, Karin Dooleweerdt, Qingle Zeng, Stephen L Buchwald.   

Abstract

A catalyst based on a new biarylphosphine ligand (3) for the Pd-catalyzed cross-coupling reactions of amides and aryl chlorides is described. This system shows the highest turnover frequencies reported to date for these reactions, especially for aryl chloride substrates bearing an ortho substituent. An array of amides and aryl chlorides were successfully reacted in good to excellent yields.

Entities:  

Year:  2009        PMID： 20740063      PMCID： PMC2927134          DOI： 10.1016/j.tet.2009.04.096

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  26 in total

1.  A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles.

Authors:  A Klapars; J C Antilla; X Huang; S L Buchwald
Journal:  J Am Chem Soc       Date:  2001-08-08       Impact factor: 15.419

2.  Efficient access to cyclic ureas via Pd-catalyzed cyclization.

Authors:  Mark McLaughlin; Michael Palucki; Ian W Davies
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

3.  Preparation of enamides via palladium-catalyzed amidation of enol tosylates.

Authors:  Artis Klapars; Kevin R Campos; Cheng-Yi Chen; Ralph P Volante
Journal:  Org Lett       Date:  2005-03-17       Impact factor: 6.005

Review 4.  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

5.  Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles.

Authors:  Dawei Ma; Qian Cai
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

6.  Pd-catalyzed amidation of aryl chlorides using monodentate biaryl phosphine ligands: a kinetic, computational, and synthetic investigation.

Authors:  Takashi Ikawa; Timothy E Barder; Mark R Biscoe; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

7.  Expanding Pd-catalyzed C-N bond-forming processes: the first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions.

Authors:  Xiaohua Huang; Kevin W Anderson; Danilo Zim; Lei Jiang; Artis Klapars; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2003-06-04       Impact factor: 15.419

8.  Synthetic approaches to the microtubule-stabilizing sponge alkaloid ceratamine A and desbromo analogues.

Authors:  Matt Nodwell; Alban Pereira; Jenna L Riffell; Carla Zimmerman; Brian O Patrick; Michel Roberge; Raymond J Andersen
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

9.  Ancisheynine, the first n,c-coupled naphthylisoquinoline alkaloid: total synthesis and stereochemical analysis.

Authors:  Gerhard Bringmann; Tanja Gulder; Matthias Reichert; Frank Meyer
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005

10.  N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with o-acetyl hydroxamic acids.

Authors:  Zhihui Zhang; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2008-06-17       Impact factor: 6.005
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  29 in total

1.  Palladium-catalyzed arylation of cyanamides.

Authors:  Ryan M Stolley; Wenxing Guo; Janis Louie
Journal:  Org Lett       Date:  2011-12-05       Impact factor: 6.005

2.  A multiligand based Pd catalyst for C-N cross-coupling reactions.

Authors:  Brett P Fors; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-27       Impact factor: 15.419

3.  Synthesis of unsymmetrical diarylureas via Pd-catalyzed C-N cross-coupling reactions.

Authors:  Simon Breitler; Nathan J Oldenhuis; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2011-05-23       Impact factor: 6.005

4.  A bulky biaryl phosphine ligand allows for palladium-catalyzed amidation of five-membered heterocycles as electrophiles.

Authors:  Mingjuan Su; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-30       Impact factor: 15.336

5.  Ligand-controlled regiodivergent palladium-catalyzed decarboxylative allylation reaction to access α,α-difluoroketones.

Authors:  Ming-Hsiu Yang; Douglas L Orsi; Ryan A Altman
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-07       Impact factor: 15.336

6.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

7.  An Improved Synthesis of BrettPhos and RockPhos-Type Biarylphosphine Ligands.

Authors:  Naoyuki Hoshiya; Stephen L Buchwald
Journal:  Adv Synth Catal       Date:  2012-06-27       Impact factor: 5.837

8.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

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.  Synthesis and application of palladium precatalysts that accommodate extremely bulky di-tert-butylphosphino biaryl ligands.

Authors:  Nicholas C Bruno; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-05-15       Impact factor: 6.005
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