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†,Organic Chemistry Frontiers

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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†
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2018-02-20 00:00:00 , DOI: 10.1039/c7qo01128h
Shi-Meng Wang _{1,

2,

3,

4,

5} , Chen Li _{1,

2,

3,

4,

5} , Jing Leng _{1,

2,

3,

4,

5} , Syed Nasir Abbas Bukhari _{1,

2,

3,

4,

5} , Hua-Li Qin _{1,

2,

3,

4,

5}

Affiliation

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.

中文翻译：

铑（iii）催化的N-甲氧基苯甲酰胺和乙磺酰氟的氧化偶联：制备2-芳基乙磺酰氟和磺酰氟取代的γ-内酰胺的CH键活化策略†

通过铑（Ⅲ）催化的N-甲氧基苯甲酰胺和乙磺酰氟（ESF）的氧化偶联，开发了一种合成2-芳基乙磺酰氟和磺酰氟取代的γ-内酰胺的方法。该方案具有独特的E-立体选择性和对苯环的sp ² C–H键的单选择性邻位活化。这项研究表明，反应性低得多的Heck偶联伴侣乙磺酰氟（ESF）具有与sp ² C–H键偶联的可能性，从而为SuFEx点击反应提供了一类新的磺酰氟支架。

更新日期：2018-02-20

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