Literature DB >> 19583200

Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides.

Wing-Yiu Yu1, Wing Nga Sit, Zhongyuan Zhou, Albert S-C Chan.   

Abstract

A Pd(OAc)(2)-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.

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Year:  2009        PMID: 19583200     DOI: 10.1021/ol900756g

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


  13 in total

1.  Direct arylation of 6-phenylpurine and 6-arylpurine nucleosides by ruthenium-catalyzed C-H bond activation.

Authors:  Mahesh K Lakshman; Ashoke C Deb; Raghu Ram Chamala; Padmanava Pradhan; Ramendra Pratap
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-28       Impact factor: 15.336

2.  On the mechanism of palladium-catalyzed aromatic C-H oxidation.

Authors:  David C Powers; Daphne Y Xiao; Matthias A L Geibel; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

3.  Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed C-H Arylation with Diaryliodonium Salts.

Authors:  Sharon R Neufeldt; Melanie S Sanford
Journal:  Adv Synth Catal       Date:  2012-12-14       Impact factor: 5.837

4.  Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

Authors:  Peter S Thuy-Boun; Giorgio Villa; Devin Dang; Paul Richardson; Shun Su; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-11-08       Impact factor: 15.419

5.  Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis.

Authors:  Dipannita Kalyani; Kate B McMurtrey; Sharon R Neufeldt; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2011-11-02       Impact factor: 15.419

6.  Surprisingly Facile C-H Activation in the Course of Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Nathan C Thacker; Veronika M Shoba; Andrew E Geis; James M Takacs
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

7.  Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids.

Authors:  Lingling Chu; Jeffrey M Lipshultz; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-26       Impact factor: 15.336

8.  Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters.

Authors:  Lingying Leng; Joseph M Ready
Journal:  ACS Catal       Date:  2021-10-27       Impact factor: 13.700

9.  Mild palladium-catalyzed C-H alkylation using potassium alkyltrifluoroborates in combination with MnF3.

Authors:  Sharon R Neufeldt; Cydney K Seigerman; Melanie S Sanford
Journal:  Org Lett       Date:  2013-04-19       Impact factor: 6.005

Review 10.  Palladium-catalyzed ligand-directed C-H functionalization reactions.

Authors:  Thomas W Lyons; Melanie S Sanford
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

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