Literature DB >> 20704334

Pd-catalyzed ortho-C-H acylation/cross coupling of aryl ketone O-methyl oximes with aldehydes using tert-butyl hydroperoxide as oxidant.

Chun-Wo Chan1, Zhongyuan Zhou, Albert S C Chan, Wing-Yiu Yu.   

Abstract

A Pd-catalyzed protocol for direct C-H bond acylation by cross coupling of aryl ketone oximes and aldehydes using tert-butyl hydroperoxide (TBHP) as oxidant was developed. With oximes as a directing group for the C-H activation, the coupling with aldehydes was achieved with remarkable regioselectivity. The acylation reactions exhibit excellent functional group tolerance, and both aliphatic and heteroaromatic aldehydes can be effectively coupled to the oximes.

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Year:  2010        PMID: 20704334     DOI: 10.1021/ol101618u

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


  7 in total

1.  Intermolecular Markovnikov-Selective Hydroacylation of Olefins Catalyzed by a Cationic Ruthenium-Hydride Complex.

Authors:  Junghwa Kim; Chae S Yi
Journal:  ACS Catal       Date:  2016-04-19       Impact factor: 13.084

2.  Palladium-Catalyzed Dearomative syn-1,4-Oxyamination.

Authors:  Conghui Tang; Mikiko Okumura; Hejun Deng; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-20       Impact factor: 15.336

3.  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

4.  Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

Authors:  Joshua R Hummel; Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

5.  Synthesis of 2-Acylphenol and Flavene Derivatives from the Ruthenium-Catalyzed Oxidative C-H Acylation of Phenols with Aldehydes.

Authors:  Hanbin Lee; Chae S Yi
Journal:  European J Org Chem       Date:  2015-03

6.  Asymmetric chiral ligand-directed alkene dioxygenation.

Authors:  Sharon R Neufeldt; Melanie S Sanford
Journal:  Org Lett       Date:  2012-12-18       Impact factor: 6.005

7.  Palladium(II)-catalyzed othro-C-H-benzoxylation of 2-arylpyridines by oxidative coupling with aryl acylperoxides.

Authors:  Wing-Nga Sit; Chun-Wo Chan; Wing-Yiu Yu
Journal:  Molecules       Date:  2013-04-15       Impact factor: 4.411

  7 in total

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