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Literature DB >> 15387557

A new ketone synthesis by palladium-catalyzed cross-coupling reactions of esters with organoboron compounds.

Hiroto Tatamidani¹, Fumitoshi Kakiuchi, Naoto Chatani.

Abstract

[reaction: see text] The palladium-catalyzed coupling reaction of 2-pyridyl esters with organoboron compounds is described. The reaction is compatible with various functional groups and proceeds under mild reaction conditions. The coordination of the nitrogen atom to Pd is a key step for efficient reaction.

Entities: Chemical

Year: 2004 PMID： 15387557 DOI： 10.1021/ol048513o

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

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Cited

21 in total

1. Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors: Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal: ACS Catal Date: 2020-09-10 Impact factor: 13.084

2. Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.

Authors: Alexander C Wotal; Daniel J Weix
Journal: Org Lett Date: 2012-02-23 Impact factor: 6.005

3. Breaking Amides using Nickel Catalysis.

Authors: Jacob E Dander; Neil K Garg
Journal: ACS Catal Date: 2017-01-06 Impact factor: 13.084

4. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors: Louis-Charles Campeau; Nilay Hazari
Journal: Organometallics Date: 2018-11-27 Impact factor: 3.876

5. Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides.

Authors: Timothy B Boit; Nicholas A Weires; Junyong Kim; Neil K Garg
Journal: ACS Catal Date: 2017-12-20 Impact factor: 13.084

6. Ambient temperature synthesis of high enantiopurity N-protected peptidyl ketones by peptidyl thiol ester-boronic acid cross-coupling.

Authors: Hao Yang; Hao Li; Rüdiger Wittenberg; Masahiro Egi; Wenwei Huang; Lanny S Liebeskind
Journal: J Am Chem Soc Date: 2007-02-07 Impact factor: 15.419

A new ketone synthesis by palladium-catalyzed cross-coupling reactions of esters with organoboron compounds.

1. Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

2. Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.

3. Breaking Amides using Nickel Catalysis.

4. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

5. Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides.

6. Ambient temperature synthesis of high enantiopurity N-protected peptidyl ketones by peptidyl thiol ester-boronic acid cross-coupling.

7. Nickel-Catalyzed Synthesis of Ketones from Alkyl Halides and Acid Chlorides: Preparation of Ethyl 4-Oxododecanoate.

8. Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles.

9. Nickel-Catalyzed Activation of Acyl C-O Bonds of Methyl Esters.

10. Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters.