Literature DB >> 18484772

Direct ortho-acetoxylation of anilides via palladium-catalyzed sp(2) C-H bond oxidative activation.

Guan-Wu Wang1, Ting-Ting Yuan, Xue-Liang Wu.   

Abstract

Various anilides have been directly ortho-acetoxylated through a Pd(OAc)2-catalyzed C-H bond activation process. The amide group in anilides was found to functionalize as an elegant directing group to convert aromatic sp(2) C-H bonds into C-O bonds in high regioselectivity with acetic acid as the acetate source and K(2)S(2)O(8) as the oxidant.

Entities:  

Year:  2008        PMID: 18484772     DOI: 10.1021/jo8003088

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  21 in total

1.  PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes.

Authors:  Natalia Chernyak; Alexander S Dudnik; Chunhui Huang; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

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.  Palladium-Catalyzed C-H Bond Acetoxylation via Electrochemical Oxidation.

Authors:  Anuska Shrestha; Melissa Lee; Anna L Dunn; Melanie S Sanford
Journal:  Org Lett       Date:  2017-12-22       Impact factor: 6.005

4.  Controlling site selectivity in palladium-catalyzed C-H bond functionalization.

Authors:  Sharon R Neufeldt; Melanie S Sanford
Journal:  Acc Chem Res       Date:  2012-05-03       Impact factor: 22.384

5.  Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group.

Authors:  Anton V Gulevich; Ferdinand S Melkonyan; Dhruba Sarkar; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2012-03-19       Impact factor: 15.419

6.  Palladium-catalyzed C-H functionalization using guanidine as a directing group: ortho arylation and olefination of arylguanidines.

Authors:  Jiaan Shao; Wenteng Chen; Marc A Giulianotti; Richard A Houghten; Yongping Yu
Journal:  Org Lett       Date:  2012-10-24       Impact factor: 6.005

7.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors:  Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2011-05-01       Impact factor: 5.837

8.  Palladium-catalyzed regioselective synthesis of 2(2'-biphenyl)benzimidazoles through C-H activation.

Authors:  Li-Hsun Chen; Tz-Yi Wu; Vijaykumar Paike; Chung-Ming Sun
Journal:  Mol Divers       Date:  2013-07-19       Impact factor: 2.943

Review 9.  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

10.  O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization.

Authors:  Sharon R Neufeldt; Melanie S Sanford
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

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