Yao Tuanli, Zhang Xiaoxia, Larock Richard C
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
J Org Chem. 2005 Sep 16;70(19):7679-85. doi: 10.1021/jo0510585.
[reaction: see text] The coupling of 2-(1-alkynyl)-2-alken-1-ones with nucleophiles, either catalyzed by AuCl3 or induced by an electrophile, provides highly substituted furans in good to excellent yields under very mild reaction conditions. Various nucleophiles, including functionally substituted alcohols, H2O, carboxylic acids, 1,3-diketones, and electron-rich arenes, and a range of cyclic and acyclic 2-(1-alkynyl)-2-alken-1-ones readily participate in these cyclizations. Iodine, NIS, and PhSeCl have proven successful as electrophiles in this process. The resulting iodine-containing furans can be readily elaborated to more complex products using known organopalladium chemistry.
[反应：见正文] 2-(1-炔基)-2-烯-1-酮与亲核试剂的偶联反应，无论是由三氯化金催化还是由亲电试剂诱导，都能在非常温和的反应条件下以良好至优异的产率提供高度取代的呋喃。各种亲核试剂，包括功能取代的醇、水、羧酸、1,3-二酮和富电子芳烃，以及一系列环状和非环状的2-(1-炔基)-2-烯-1-酮都很容易参与这些环化反应。在这个过程中，碘、N-碘代琥珀酰亚胺和苯基硒氯已被证明是成功的亲电试剂。使用已知的有机钯化学方法，可以很容易地将所得的含碘呋喃转化为更复杂的产物。
