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Silver-Catalyzed C-to N-Center Radical Remote arene migration of Alkynes

Silver-Catalyzed C-to N-Center Radical Remote Arene Migratio...

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中国化学会·第十五届全国有机合成化学学术研讨会

作者： Yongquan Ning 毕锡和 Department of Chemistry Northeast Normal University 东北师范大学

The development of selective C–C bond cleavage processes has been attracting much attention in organic *** advances have been achieved on the selective functionalization of C-C bonds in both strained and unstrained molecules, and migrations between carbon centers by transfer of functional groups to proximal carbon-centered radicals, cations, and carbenes have become well-established. Among these, significant progress has been reported for radical-mediated group migrations between carbon centers using unsaturated substrates. Mechanistically, a common reaction pathway is observed involving initiation of the reaction by radical addition to the unsaturated systems to generate a C-radical intermediate, which proceed through radical ipso substitution followed by C-C cleavage(Figure 1a).However, there have been no studies on aryl migration from carbon to a nitrogen center using unsaturated substrates, probably due to the lack of versatile radical initiation methods to produce N-center radicals, and indeed carbon-to-nitrogen remote aryl migration is rare in general. Building on our interests in silver-catalyzed alkyne activation, we report herein a mild, silver-catalyzed C-center to N-center radical-mediated remote arene migration reaction of homopropargylic alcohols, employing TMSN as the nitrogen atom source, and sodium sulfinates as radical generators(Figure 1b).To the best of our knowledge, this is the first example of aryl migration from C-to N-center using alkynes as substrates.

关键词： silver catalysis arene migration radical alkynes N-center

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