Rhodium(iii)-catalyzed Oxidative Coupling of: N -Methoxybenzamides and Ethenesulfonyl fluoride: A C-H Bond Activation Strategy for the Preparation of 2-Aryl ethenesulfonyl fluorides and Sulfonyl fluoride Substituted γ-Lactams

Shi Meng Wang, Chen Li, Jing Leng, Bukhari Syed Nasir Abbas, Hua Li Qin

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

A method for the synthesis of 2-aryl ethenesulfonyl fluorides and sulfonyl fluoride substituted γ-lactams was developed through a rhodium(iii)-catalyzed oxidative coupling of N-methoxybenzamides and ethenesulfonyl fluoride (ESF) in moderate to excellent yields. This protocol featured an exclusive E-stereo selectivity and a monoselective ortho activation of sp2 C-H bonds of the phenyl rings. This research revealed that the much less reactive Heck coupling partner ethenesulfonyl fluoride (ESF) possesses the feasibility for coupling with sp2 C-H bonds to provide a class of new sulfonyl fluoride scaffolds for the SuFEx click reaction.

Original languageEnglish
Pages (from-to)1411-1415
Number of pages5
JournalOrganic Chemistry Frontiers
Volume5
Issue number9
DOIs
Publication statusPublished - 1 Jan 2018
Externally publishedYes

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Lactams
Rhodium
Fluorides
Chemical activation
Stereoselectivity
Scaffolds
sulfuryl fluoride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Rhodium(iii)-catalyzed Oxidative Coupling of : N -Methoxybenzamides and Ethenesulfonyl fluoride: A C-H Bond Activation Strategy for the Preparation of 2-Aryl ethenesulfonyl fluorides and Sulfonyl fluoride Substituted γ-Lactams. / Wang, Shi Meng; Li, Chen; Leng, Jing; Syed Nasir Abbas, Bukhari; Qin, Hua Li.

In: Organic Chemistry Frontiers, Vol. 5, No. 9, 01.01.2018, p. 1411-1415.

Research output: Contribution to journalArticle

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