Literature DB >> 30156857

Remote Site-Specific Radical Alkynylation of Unactivated C-H Bonds.

Lin Wang1, Yong Xia1, Klaus Bergander1, Armido Studer1.   

Abstract

A method for remote radical C-H alkynylation at unactivated sites is reported. C-H functionalization proceeds via 1,5-hydrogen atom transfer (HAT) to amidyl radicals that are generated via an addition/fragmentation reaction. The readily installed N-allylsulfonyl moiety is used as a precursor of the N-centered radical. Unactivated secondary and tertiary as well as selected primary C-H bonds can be functionalized by this method.

Entities:  

Year:  2018        PMID： 30156857     DOI： 10.1021/acs.orglett.8b02514

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


  7 in total

1.  Radical 1,2,3-tricarbofunctionalization of α-vinyl-β-ketoesters enabled by a carbon shift from an all-carbon quaternary center.

Authors:  Qi Zhang; Mong-Feng Chiou; Changqing Ye; Xiaobin Yuan; Yajun Li; Hongli Bao
Journal:  Chem Sci       Date:  2022-05-02       Impact factor: 9.969

2.  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

3.  Copper-catalyzed remote C(sp3)-H azidation and oxidative trifluoromethylation of benzohydrazides.

Authors:  Xu Bao; Qian Wang; Jieping Zhu
Journal:  Nat Commun       Date:  2019-02-15       Impact factor: 14.919

Review 4.  Alkynylation of radicals: spotlight on the "Third Way" to transfer triple bonds.

Authors:  Franck Le Vaillant; Jérôme Waser
Journal:  Chem Sci       Date:  2019-08-13       Impact factor: 9.825

5.  Functionalization of remote C(sp3)-H bonds enabled by copper-catalyzed coupling of O-acyloximes with terminal alkynes.

Authors:  Zhaodong Li; Rubén O Torres-Ochoa; Qian Wang; Jieping Zhu
Journal:  Nat Commun       Date:  2020-01-21       Impact factor: 14.919

6.  Divergent functionalization of aldehydes photocatalyzed by neutral eosin Y with sulfone reagents.

Authors:  Jianming Yan; Haidi Tang; Eugene Jun Rong Kuek; Xiangcheng Shi; Chenguang Liu; Muliang Zhang; Jared L Piper; Shengquan Duan; Jie Wu
Journal:  Nat Commun       Date:  2021-12-10       Impact factor: 14.919

7.  Radical 1-Fluorosulfonyl-2-alkynylation of Unactivated Alkenes.

Authors:  Nils Lennart Frye; Constantin G Daniliuc; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2022-01-27       Impact factor: 16.823
  7 in total

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