Palladium-Catalyzed Tandem Dehydrogenative [4 + 2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C–H Activations,Organic Letters

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Palladium-Catalyzed Tandem Dehydrogenative [4 + 2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C–H Activations
Organic Letters ( IF 4.9 ) Pub Date : 2020-03-27 , DOI: 10.1021/acs.orglett.0c01011
Manman Sun ₁ , Weida Chen ₁ , Xiangyu Xia ₁ , Guodong Shen ₂ , Yongmin Ma ₁ , Jianguo Yang ₁ , Hanfeng Ding ₃ , Zhiming Wang ₁

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A palladium-catalyzed tandem dehydrogenative [4 + 2] annulation of terminal olefins with N-sulfonyl amides via C(sp²)–H activation, allylic C(sp³)–H activation, and homoallylic C(sp³)–H elimination processes has been developed. Promoted by the DMSO ligand, various benzamides, heterocyclic arylamides, alkenyl carboxamides, and commercial olefins are found to be efficient substrates to construct important heterocyclic compounds bearing a vinyl substituent with high E stereoselectivity. Using air as the terminal oxidant also provides a great advantage regarding environmental friendliness.

中文翻译：

钯催化串联脱氢[4 + 2]通过C–H活化与N-磺酰胺形成末端烯烃

通过C（sp ²）–H活化，烯丙基C（sp ³）–H活化和均烯丙基C（sp ³）–H消除，钯催化串联脱氢[4 + 2]与N-磺酰胺酰胺化末端烯烃流程已开发。发现在DMSO配体的促进下，各种苯甲酰胺，杂环芳基酰胺，烯基羧酰胺和商业烯烃是构建具有高E立体选择性的带有乙烯基取代基的重要杂环化合物的有效底物。使用空气作为终端氧化剂在环境友好方面也提供了很大的优势。

更新日期：2020-04-24

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