School of Pharmaceutical Sciences , Sun Yat-sen University , Guangzhou 510006 , China.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science , Soochow University , Suzhou 215123 , China.
Org Lett. 2018 Sep 7;20(17):5332-5335. doi: 10.1021/acs.orglett.8b02251. Epub 2018 Aug 27.
A novel gold-catalyzed water-mediated carbene cascade reaction of propargyl diazoacetates has been developed. Mechanistic investigation indicates that this reaction is initiated by gold-catalyzed gold-carbene formation followed by an unprecedented 6- endo-dig carbocyclization with tethered alkyne through an oxonium ylide intermediate, terminated by a β-H elimination/protodeauration process to give the aromatized furan products in good to high yields with broad substrate generality. Notably, the proposed gold-carbene intermediates are verified by interception experiments.
一种新型的金催化水介导的偕二氮丙酸盐卡宾级联反应已经被开发出来。机理研究表明，该反应是由金催化的金卡宾形成引发的，随后通过氧翁叶立德中间体进行了前所未有的 6-endo-dig 碳环化反应，与桥连炔烃反应，通过β-H 消除/脱金过程终止，得到了芳香化呋喃产物，产率良好至高产，具有广泛的底物通用性。值得注意的是，通过截获实验验证了所提出的金卡宾中间体。
