Pd(II)-Catalyzed Carbonyl-Directing Activation of Alkenes: Selective Fluorosulfonylation and Aminosulfonylation of 1,7-Enynes

Yi Long Zhu, Chi Fan Zhu, Peng Zhou, Wen Juan Hao, De Cai Wang, Shu Jiang Tu, Bo Jiang

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Abstract

A new Pd(II)-catalyzed carbonyl-directing activation of alkenes has been established, enabling radical-induced selective fluorosulfonylation and aminosulfonylation of carbonyl-tethered 1,7-enynes with sulfinic acids and N-fluorobenzenesulfonimide (NFSI) under mild and redox neutral conditions to access densely functionalized (E)-3,4-dihydronaphthalen-1(2H)-ones with generally good yields and high stereoselectivity. The selectivity of these bifunctionalizations relies on the electronic nature of substituents on both aryl rings of 1,7-enynes.

Original languageEnglish
Pages (from-to)9641-9653
Number of pages13
JournalJournal of Organic Chemistry
Volume83
Issue number17
DOIs
StatePublished - 7 Sep 2018

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