Wang Hong-Fa, Guo Lin-Na, Fan Zhi-Bo, Tang Tian-Hua, Zi Weiwei
State Key Laboratory and Institute of Elemento-Organic Chemistry and College of Chemistry, Nankai University, Tianjin, 300071, China.
Org Lett. 2021 Apr 2;23(7):2676-2681. doi: 10.1021/acs.orglett.1c00581. Epub 2021 Mar 15.
A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.
报道了一种双金催化的六脱氢狄尔斯-阿尔德/碳烷氧基化串联反应。在该转化过程中，金催化剂参与六脱氢狄尔斯-阿尔德步骤，将反应机理从自由基型转变为阳离子型，然后催化剂活化生成的芳炔以形成邻位金苯基阳离子物种，该物种发生碳烷氧基化重排而非预期的芳炔-烯反应。
