Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul 133-791, Korea.
J Org Chem. 2011 Sep 2;76(17):7204-15. doi: 10.1021/jo201339z. Epub 2011 Aug 8.
Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the π-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.
发展了一种金(I)催化的烯基羰基化合物环化反应,得到了多种取代的萘。该过程利用了金(I)催化剂的双重功能:(1)金(I)催化剂的亲氧性,与通常与 Au 催化剂相关的π-酸性反应性相反;(2)支持通过同位素混合实验的结果进行烯烃异构化。不能完全排除在该方案中 TfOH 是真正的有效催化剂。考虑到实际情况,此反应中对非立体纯起始原料的需求特别有吸引力和价值。