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Literature DB >> 19072215

Palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands.

David X Yang¹, Steven L Colletti, Kevin Wu, Maoying Song, George Y Li, Hong C Shen.

Abstract

The palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters provided an efficient approach to useful biaryl building blocks containing a 2-pyridyl moiety. The convenient reaction protocol demonstrates its potentially wide applications in medicinal chemistry.

Entities: Chemical

Mesh：

Substances：

Year: 2009 PMID： 19072215 DOI： 10.1021/ol802642g

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

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Cited

14 in total

1. Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

Authors: Beryl X Li; Diane N Le; Kyle A Mack; Andrew McClory; Ngiap-Kie Lim; Theresa Cravillion; Scott Savage; Chong Han; David B Collum; Haiming Zhang; Francis Gosselin
Journal: J Am Chem Soc Date: 2017-07-26 Impact factor: 15.419

2. A versatile catalyst system for Suzuki-Miyaura cross-coupling reactions of C(sp(2))-tosylates and mesylates.

Authors: Brijesh Bhayana; Brett P Fors; Stephen L Buchwald
Journal: Org Lett Date: 2009-09-03 Impact factor: 6.005

3. Development of a palladium-catalyzed decarboxylative cross-coupling of (2-azaaryl)carboxylates with aryl halides.

Authors: Christopher K Haley; Christopher D Gilmore; Brian M Stoltz
Journal: Tetrahedron Date: 2013-07-08 Impact factor: 2.457

4. Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions.

Authors: James R Colombe; Sebastian Bernhardt; Christos Stathakis; Stephen L Buchwald; Paul Knochel
Journal: Org Lett Date: 2013-10-24 Impact factor: 6.005

5. A general method for Suzuki-Miyaura coupling reactions using lithium triisopropyl borates.

Authors: Matthias A Oberli; Stephen L Buchwald
Journal: Org Lett Date: 2012-08-15 Impact factor: 6.005

6. Design, Synthesis, and Application of Polymer-Supported Silicon-Transfer Agents for Cross-Coupling Reactions with Organolithium Reagents.

Authors: Minh H Nguyen; Kevin T O'Brien; Amos B Smith
Journal: J Org Chem Date: 2017-10-02 Impact factor: 4.354

Palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands.

1. Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

2. A versatile catalyst system for Suzuki-Miyaura cross-coupling reactions of C(sp(2))-tosylates and mesylates.

3. Development of a palladium-catalyzed decarboxylative cross-coupling of (2-azaaryl)carboxylates with aryl halides.

4. Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions.

5. A general method for Suzuki-Miyaura coupling reactions using lithium triisopropyl borates.

6. Design, Synthesis, and Application of Polymer-Supported Silicon-Transfer Agents for Cross-Coupling Reactions with Organolithium Reagents.

7. General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates.

8. Palladium-catalyzed 1,1-difunctionalization of ethylene.

9. A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.

10. Mild and general conditions for negishi cross-coupling enabled by the use of palladacycle precatalysts.