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Literature DB >> 18620415

Water-mediated catalyst preactivation: an efficient protocol for C-N cross-coupling reactions.

Brett P Fors¹, Philipp Krattiger, Eric Strieter, Stephen L Buchwald.

Abstract

A protocol for forming a highly active Pd(0) catalyst from n class="Chemical">Pd(OAc) 2, water, and biaryldialkylphosphine ligands has been developed. This protocol generates a catalyst system, which exhibits excellent reactivity and efficiency in the coupling of a variety of amides and anilines with aryl chlorides.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 18620415 PMCID： PMC2948866 DOI： 10.1021/ol801285g

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

13 in total

1. Highly active, air-stable versatile palladium catalysts for the C-C, C-N, and C-S bond formations via cross-coupling reactions of aryl chlorides.

Authors: G Y Li; G Zheng; A F Noonan
Journal: J Org Chem Date: 2001-12-14 Impact factor: 4.354

2. A new generation of air stable, highly active Pd complexes for C--C and C--N coupling reactions with aryl chlorides.

Authors: Anita Schnyder; Adriano F Indolese; Martin Studer; Hans-Ulrich Blaser
Journal: Angew Chem Int Ed Engl Date: 2002-10-04 Impact factor: 15.336

3. Unparalleled rates for the activation of aryl chlorides and bromides: coupling with amines and boronic acids in minutes at room temperature.

Authors: James P Stambuli; Ryoichi Kuwano; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2002-12-16 Impact factor: 15.336

4. An air and thermally stable one- component catalyst for the amination of aryl chlorides.

Authors: Danilo Zim; Stephen L Buchwald
Journal: Org Lett Date: 2003-07-10 Impact factor: 6.005

5. Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles.

Authors: Darcy A Culkin; John F Hartwig
Journal: Acc Chem Res Date: 2003-04 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. Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions.

Authors: Nicolas Marion; Oscar Navarro; Jianguo Mei; Edwin D Stevens; Natalie M Scott; Steven P Nolan
Journal: J Am Chem Soc Date: 2006-03-29 Impact factor: 15.419

9. New ligands for a general palladium-catalyzed amination of aryl and heteroaryl chlorides.

Authors: Franck Rataboul; Alexander Zapf; Ralf Jackstell; Surendra Harkal; Thomas Riermeier; Axel Monsees; Uwe Dingerdissen; Matthias Beller
Journal: Chemistry Date: 2004-06-21 Impact factor: 5.236

10. Electronic effects on reductive elimination to form carbon-carbon and carbon-heteroatom bonds from palladium(II) complexes.

Authors: John F Hartwig
Journal: Inorg Chem Date: 2007-03-19 Impact factor: 5.165

29 in total

1. Me3(OMe)tBuXPhos: a surrogate ligand for Me4tBuXPhos in palladium-catalyzed C-N and C-O bond-forming reactions.

Authors: Satoshi Ueda; Siraj Ali; Brett P Fors; Stephen L Buchwald
Journal: J Org Chem Date: 2012-02-15 Impact factor: 4.354

2. Palladium-triggered deprotection chemistry for protein activation in living cells.

Authors: Jie Li; Juntao Yu; Jingyi Zhao; Jie Wang; Siqi Zheng; Shixian Lin; Long Chen; Maiyun Yang; Shang Jia; Xiaoyu Zhang; Peng R Chen
Journal: Nat Chem Date: 2014-03-16 Impact factor: 24.427

3. An improved protocol for the Pd-catalyzed alpha-arylation of aldehydes with aryl halides.

Authors: Rubén Martín; Stephen L Buchwald
Journal: Org Lett Date: 2008-09-23 Impact factor: 6.005

4. 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

5. Palladium(0)-catalyzed arylative dearomatization of phenols.

Authors: Sophie Rousseaux; Jorge García-Fortanet; Miguel Angel Del Aguila Sanchez; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2011-05-25 Impact factor: 15.419

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. Application of Suzuki-Miyaura and Buchwald-Hartwig Cross-coupling Reactions to the Preparation of Substituted 1,2,4-Benzotriazine 1-Oxides Related to the Antitumor Agent Tirapazamine.

Authors: Ujjal Sarkar; Roman Hillebrand; Kevin M Johnson; Andrea H Cummings; Ngoc Linh Phung; Anuruddha Rajapakse; Haiying Zhou; Jordan R Willis; Charles L Barnes; Kent S Gates
Journal: J Heterocycl Chem Date: 2015-11-25 Impact factor: 2.193

8. 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

9. 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

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