Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan ROC.
Org Lett. 2016 Aug 5;18(15):3758-61. doi: 10.1021/acs.orglett.6b01781. Epub 2016 Jul 19.
An efficient protocol for the synthesis of highly functionalized furans via intramolecular Wittig reaction has been developed using catalytic amounts of phosphine and triethylamine. Silyl chloride served as the initial promoter to activate the phosphine oxide. Reduction of the activated phosphine oxide by hydrosilane resulted in generation of phosphine, while decomposition of Et3N·HCl resulted in regeneration of base, which mediated formation of phosphorus ylide. Remarkably, the in situ generated byproduct, Et3N·HCl, also catalyzes reduction of phosphine oxide.
本文采用催化量的膦和三乙胺开发了一种通过分子内 Wittig 反应高效合成高度官能化呋喃的方法。三氯硅烷作为初始促进剂来活化氧化膦。硅烷还原活化的氧化膦生成膦，同时 Et3N·HCl 分解生成再生碱，这促进了磷叶立德的形成。值得注意的是，原位生成的副产物 Et3N·HCl 也可以催化氧化膦的还原。
