Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides.

Literature DB >> 18447360

A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides.

Mark R Biscoe¹, Brett P Fors, Stephen L Buchwald.

Abstract

A new class of one-component Pd precatalysts bearing biarylphosphine ligands is described. These precatalysts are air- and thermally stable, are easily activated under normal reaction conditions at or below room temperature, and ensure the formation of the highly active monoligated Pd(0) complex necessary for oxidative addition. The use of these precatalysts as a convenient source of LPd(0) in C-N cross-coupling reactions is explored. The reactivity that is demonstrated in this study is unprecedented in palladium chemistry.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2008 PMID： 18447360 PMCID： PMC2587037 DOI： 10.1021/ja801137k

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

10 in total

1. 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

2. Improved functional group compatibility in the palladium-catalyzed synthesis of aryl amines.

Authors: Michele C Harris; Xiaohua Huang; Stephen L Buchwald
Journal: Org Lett Date: 2002-08-22 Impact factor: 6.005

3. 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

4. An extremely active catalyst for the Negishi cross-coupling reaction.

Authors: Jacqueline E Milne; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2004-10-13 Impact factor: 15.419

5. Pd-catalyzed Kumada-Corriu cross-coupling reactions at low temperatures allow the use of Knochel-type Grignard reagents.

Authors: Ruben Martin; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2007-03-13 Impact factor: 15.419

6. Electronic effects on the selectivity of pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: the competitive roles of amine binding and acidity.

Authors: Mark R Biscoe; Timothy E Barder; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

7. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors: Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

8. 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

9. 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

10. Eta2-dba complexes of Pd(0): the substituent effect in Suzuki-Miyaura coupling.

Authors: Ian J S Fairlamb; Anant R Kapdi; Adam F Lee
Journal: Org Lett Date: 2004-11-25 Impact factor: 6.005

10 in total

62 in total

8. tBu₃P-Coordinated 2-Phenylaniline-Based Palladacycle Complex As Precatalyst for Pd-Catalyzed Coupling Reactions of Aryl Halides with Polyfluoroarenes via C-H Activation Strategy.

Authors: Hong-Hai Zhang; Jie Dong; Qiao-Sheng Hu
Journal: European J Org Chem Date: 2014-02-01

9. 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

Review 10. Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution.

Authors: Yike Zou; Amos B Smith
Journal: J Antibiot (Tokyo) Date: 2017-08-30 Impact factor: 2.649

A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides.

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

2. Improved functional group compatibility in the palladium-catalyzed synthesis of aryl amines.

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

4. An extremely active catalyst for the Negishi cross-coupling reaction.

5. Pd-catalyzed Kumada-Corriu cross-coupling reactions at low temperatures allow the use of Knochel-type Grignard reagents.

6. Electronic effects on the selectivity of pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: the competitive roles of amine binding and acidity.

7. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

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

9. Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions.

10. Eta2-dba complexes of Pd(0): the substituent effect in Suzuki-Miyaura coupling.

1. Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

2. Pd-catalyzed arylation of linear and angular spirodiamine salts under aerobic conditions.

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

4. Simple, Efficient Protocols for the Pd-Catalyzed Cross-Coupling Reaction of Aryl Chlorides and Dimethylamine.

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

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

7. Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.

8. tBu₃P-Coordinated 2-Phenylaniline-Based Palladacycle Complex As Precatalyst for Pd-Catalyzed Coupling Reactions of Aryl Halides with Polyfluoroarenes via C-H Activation Strategy.

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

Review 10. Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution.