Literature DB >> 25603885

Pd-catalyzed α-selective C(sp3)-H acetoxylation of amides through an unusual cyclopalladation mechanism.

Meining Wang1, Yang Yang, Zhoulong Fan, Zhen Cheng, Weiliang Zhu, Ao Zhang.   

Abstract

We report the first example of Pd-catalyzed site-selective α-C(sp(3))-H oxidation/acetoxylation of amides through an unusual [4,6]-bicyclic metallacycle intermediate with 1-aminoanthraquinone as a new bidentate directing group. In addition to the distinct mechanism and high efficiency, the reaction is highly appealing due to the ample commercial source, low-cost, as well as easy removal and recycling of the auxiliary group.

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Year:  2015        PMID： 25603885     DOI： 10.1039/c4cc09576f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  4 in total

Review 1.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

2.  Metal-Free Direct Amidation of Naphthoquinones Using Hydroxamic Acids as an Amide Source: Application in the Synthesis of an HDAC6 Inhibitor.

Authors:  Cheng Zhang; C James Chou
Journal:  Org Lett       Date:  2016-10-19       Impact factor: 6.005

Review 3.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

4.  A dual role for acetohydrazide in Pd-catalyzed controlled C(sp3)-H acetoxylation of aldehydes.

Authors:  Juan Chen; Chaolumen Bai; XingWen Tong; Dan Liu; Yong-Sheng Bao
Journal:  RSC Adv       Date:  2020-03-25       Impact factor: 3.361
  4 in total

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