Literature DB >> 26248184

Visible light mediated efficient oxidative benzylic sp(3) C-H to ketone derivatives obtained under mild conditions using O2.

Hong Yi1, Changliang Bian, Xia Hu, Linbin Niu, Aiwen Lei.   

Abstract

A photooxygenation of benzylic sp(3) C-H reaction has been demonstrated using O2 mediated by visible light. This protocol provides a simple and mild route to obtain ketones from benzylic sp(3) C-H bonds. Various benzylic sp(3) C-H bonds can be transformed into the desired ketone derivatives in moderate to good yields. The (18)O2 labelling experiments demonstrated that the oxygen introduced into ketone originated from dioxygen. A plausible mechanism has been proposed accordingly.

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Year:  2015        PMID: 26248184     DOI: 10.1039/c5cc06015j

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


  8 in total

1.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

2.  Combined Photoredox/Enzymatic C-H Benzylic Hydroxylations.

Authors:  Rick C Betori; Catherine M May; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-26       Impact factor: 15.336

3.  Copper-catalyzed C-H acyloxylation of 2-phenylpyridine using oxygen as the oxidant.

Authors:  Feifan Wang; Zhiyang Lin; Weisheng Yu; Qingdong Hu; Chao Shu; Wu Zhang
Journal:  RSC Adv       Date:  2018-05-03       Impact factor: 3.361

4.  Photo-induced oxidant-free oxidative C-H/N-H cross-coupling between arenes and azoles.

Authors:  Linbin Niu; Hong Yi; Shengchun Wang; Tianyi Liu; Jiamei Liu; Aiwen Lei
Journal:  Nat Commun       Date:  2017-02-01       Impact factor: 14.919

5.  Synthesis of Xanthones, Thioxanthones and Acridones by a Metal-Free Photocatalytic Oxidation Using Visible Light and Molecular Oxygen.

Authors:  Alejandro Torregrosa-Chinillach; Rafael Chinchilla
Journal:  Molecules       Date:  2021-02-12       Impact factor: 4.411

6.  Metal-free direct alkylation of unfunctionalized allylic/benzylic sp3 C-H bonds via photoredox induced radical cation deprotonation.

Authors:  Rong Zhou; Haiwang Liu; Hairong Tao; Xingjian Yu; Jie Wu
Journal:  Chem Sci       Date:  2017-04-28       Impact factor: 9.825

7.  The cumene/O2 system: a very simple tool for the radical chain oxidation of some functional groups.

Authors:  A Malekafzali; K Malinovska; F W Patureau
Journal:  New J Chem       Date:  2017-06-30       Impact factor: 3.591

8.  Late-stage trifluoromethylthiolation of benzylic C-H bonds.

Authors:  Wentao Xu; Wenliang Wang; Tao Liu; Jin Xie; Chengjian Zhu
Journal:  Nat Commun       Date:  2019-10-25       Impact factor: 14.919

  8 in total

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