Literature DB >> 34013927

Visible light photoredox-catalysed remote C-H functionalisation enabled by 1,5-hydrogen atom transfer (1,5-HAT).

Weisi Guo1, Qian Wang2, Jieping Zhu2.   

Abstract

The generation of heteroatom-centred radicals (X˙), followed by intramolecular 1,5-hydrogen atom transfer (1,5-HAT) and the functionalisation of the translocated carbon-centred radicals, is the basic mechanism of the classic Hofmann-Löffler-Freytag (HLF) reaction and the Barton reaction. The chemoselectivity of the 1,5-HAT process is different from that of the transition metal-catalysed counterpart, providing, therefore, a complementary tool for remote C(sp3)-H bond functionalisation. There is a recent resurgence in this research field due to the emergence of visible light photocatalysis. This tutorial review summarises the recent progress in the remote functionalisation of C-H bonds featuring a key 1,5-HAT step with particular focus on photoredox-catalyzed remote C-H functionalisation.

Entities:  

Year:  2021        PMID: 34013927     DOI: 10.1039/d0cs00774a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  8 in total

1.  Site-selective coupling of remote C(sp3)-H/meta-C(sp2)-H bonds enabled by Ru/photoredox dual catalysis and mechanistic studies.

Authors:  Hong-Chao Liu; Xiangtao Kong; Xiao-Ping Gong; Yuke Li; Zhi-Jie Niu; Xue-Ya Gou; Xue-Song Li; Yu-Zhao Wang; Wei-Yu Shi; Yan-Chong Huang; Xue-Yuan Liu; Yong-Min Liang
Journal:  Chem Sci       Date:  2022-04-12       Impact factor: 9.969

2.  Directed Ni-Catalyzed Reductive Arylation of Aliphatic C-H Bonds.

Authors:  Zhi-Yun Liu; Silas P Cook
Journal:  Org Lett       Date:  2022-05-02       Impact factor: 6.072

3.  Photoinduced metal-free borylation of aryl halides catalysed by an in situ formed donor-acceptor complex.

Authors:  Manhong Li; Siqi Liu; Haoshi Bao; Qini Li; Yi-Hui Deng; Tian-Yu Sun; Leifeng Wang
Journal:  Chem Sci       Date:  2022-04-04       Impact factor: 9.969

4.  Remote Radical Desaturation of Unactivated C-H Bonds in Amides.

Authors:  Yong Xia; Kalipada Jana; Armido Studer
Journal:  Chemistry       Date:  2021-10-08       Impact factor: 5.020

5.  Dimerizing cascades of enallenamides reveal the visible-light-promoted activation of cumulated C-C double bonds.

Authors:  Andrea Serafino; Maurizio Chiminelli; Davide Balestri; Luciano Marchiò; Franca Bigi; Rai-Mondo Maggi; Max Malacria; Giovanni Maestri
Journal:  Chem Sci       Date:  2022-01-26       Impact factor: 9.825

6.  Highly selective single and multiple deuteration of unactivated C(sp3)-H bonds.

Authors:  Nian Li; Jinhang Li; Mingzhe Qin; Jiajun Li; Jie Han; Chengjian Zhu; Weipeng Li; Jin Xie
Journal:  Nat Commun       Date:  2022-07-22       Impact factor: 17.694

7.  [3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer.

Authors:  Siya Le; Ji Li; Jian Feng; Zuxiao Zhang; Yihui Bai; Zheliang Yuan; Gangguo Zhu
Journal:  Nat Commun       Date:  2022-08-12       Impact factor: 17.694

8.  Photo-Induced Ruthenium-Catalyzed Double Remote C(sp2 )-H / C(sp3 )-H Functionalizations by Radical Relay.

Authors:  Yulei Wang; Shan Chen; Xinran Chen; Agnese Zangarelli; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-10       Impact factor: 16.823

  8 in total

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