Literature DB >> 30924672

gem-Difluoroallylation of Aryl Diazoesters via Catalyst-Free, Blue-Light-Mediated Formal Doyle-Kirmse Reaction.

Jianhua Yang1, Jiazhuang Wang1, Hongtai Huang1, Guiping Qin1, Yubo Jiang1, Tiebo Xiao1.   

Abstract

A first example of low-energy blue-light-mediated formal Doyle-Kirmse reaction for gem-difluoroallylation of aryl diazoesters has been developed. A variety of highly functionalized gem-difluoroallyl containing esters bearing transformable sulfur and bromine groups were efficiently assembled with broad substrate scope under mild, catalyst-free, and additive-free conditions. The reaction represents a practical and environmentally friendly approach for C-CF2 bond formation based on rearrangement strategy, which will find potential applications among drug discovery and development.

Entities:  

Year:  2019        PMID: 30924672     DOI: 10.1021/acs.orglett.9b00647

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


  7 in total

1.  Rhodium-catalyzed cascade reactions of triazoles with organoselenium compounds - a combined experimental and mechanistic study.

Authors:  Fang Li; Chao Pei; Rene M Koenigs
Journal:  Chem Sci       Date:  2021-03-24       Impact factor: 9.825

2.  Photochemical ring expansion reactions: synthesis of tetrahydrofuran derivatives and mechanism studies.

Authors:  Sripati Jana; Zhen Yang; Chao Pei; Xinfang Xu; Rene M Koenigs
Journal:  Chem Sci       Date:  2019-09-06       Impact factor: 9.825

3.  Light-induced metal-free transformations of unactivated pyridotriazoles.

Authors:  Ziyan Zhang; Dongari Yadagiri; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2019-07-25       Impact factor: 9.825

4.  Photocatalytic gem-Difluoroolefination Reactions by a Formal C-C Coupling/Defluorination Reaction with Diazoacetates.

Authors:  Fang Li; Chao Pei; Rene M Koenigs
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-09       Impact factor: 16.823

5.  Stoichiometric Photochemical Carbene Transfer by Bamford-Stevens Reaction.

Authors:  Sripati Jana; Fang Li; Claire Empel; Dennis Verspeek; Polina Aseeva; Rene M Koenigs
Journal:  Chemistry       Date:  2020-02-21       Impact factor: 5.236

6.  Visible Light Induced Metal-Free Carbene N-Carbazolation.

Authors:  Claire Empel; Frederic W Patureau; Rene M Koenigs
Journal:  J Org Chem       Date:  2019-08-15       Impact factor: 4.354

Review 7.  Recent Perspectives on Rearrangement Reactions of Ylides via Carbene Transfer Reactions.

Authors:  Sripati Jana; Yujing Guo; Rene M Koenigs
Journal:  Chemistry       Date:  2020-10-29       Impact factor: 5.236

  7 in total

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