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The Ketene-Surrogate Coupling: Catalytic Conversion of Aryl Iodides into Aryl Ketenes through Ynol Ethers†
Angewandte Chemie Pub Date : 27 June 2014 , DOI: 10.1002/ange.201405036
Wenhan Zhang , Joseph M. Ready

tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.

中文翻译:

烯酮代理项偶联:芳基碘的催化转化成芳基烯酮通过Ynol醚

已显示叔丁氧基乙炔与芳基碘化物进行Sonogashira偶联,生成芳基取代的叔丁基炔醇醚。这些中间体参与[1,5]氢化物转移,这导致异丁烯的挤出和芳基烯酮的生成。烯酮被多种亲核试剂原位捕获或经历了环的闭环反应,生成了羟基萘和喹啉。
更新日期:2017-01-31
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