烯酮替代偶联：通过烯醇醚将芳基碘化物催化转化为芳基烯酮。
The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.
作者信息
Zhang Wenhan, Ready Joseph M
机构信息
Department of Biochemistry, Division of Chemistry, UT Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, TX 75390-0938 (USA) http://www4.utsouthwestern.edu/readylab/index.htm.
出版信息
Angew Chem Int Ed Engl. 2014 Aug 18;53(34):8980-4. doi: 10.1002/anie.201405036. Epub 2014 Jun 27.
Abstract
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.
摘要
叔丁氧基乙炔被证明能与芳基碘发生Sonogashira偶联反应，生成芳基取代的叔丁基炔醇醚。这些中间体参与[1,5]-氢迁移，导致异丁烯的挤出并生成芳基烯酮。烯酮可与多种亲核试剂原位捕获，或进行电环化闭环反应生成羟基萘和喹啉。
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