光诱导原子经济的迭代型末端炔烃氢三氟甲基化和远程C(sp^3)-H键官能团化（英文）  

Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp^3)-H Functionalization

作　　者：刘涛 屈川华 谢劲 朱成建[1,2] Liu Tao;Qu Chuanhua;Xie Jin;Zhu Chengjian(School of Chemistry and Chemical Engineering,Nanjing University,Nanjing 210023;State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Shanghai 200032)

机构地区：[1]南京大学化学化工学院,南京210023 [2]金属有机化学国家重点实验室上海有机化学研究所,上海200032

出　　处：《有机化学》2019年第6期1613-1622,共10页Chinese Journal of Organic Chemistry

基　　金：Project supported by the National Natural Science Foundation of China(Nos.21702098,21732003,21672099);the 1000-Youth Talents Plan;the Open Training Program of Undergraduate Organic Experiment Course~~

摘　　要：使用Togni试剂的三氟甲基化反应通常会产生等物质的量的邻碘苯酸作为副产物.使用Togni试剂作为双官能团化试剂,通过氢原子转移的策略开发了一种可见光诱导的、原子和步骤经济的芳香炔的氢三氟甲基化与远程的α-C(sp3)-H的苯甲酸化接力反应.这两种转化的结合,不仅实现了100%的原子转化率,而且解决了芳香炔氢三氟甲基化的区域选择性问题.这一新型的策略提供了制备一系列高官能团化的含三氟甲基烯烃的重要途径.Trifluoromethylation using Togni reagents usually releases one equivalent of iodobenzoats as wasteful byproducts.A visible-light-mediated,atom-and step-economical hydrotrifluoromethylation of aromatic alkynes and remote benzoyl-oxylation ofα-C(sp3)-H bond of ether with Togni reagent as a bifunctional reagent by means of hydrogen atom transfer strategy was disclosed.The combination of two organic transformations into one reaction not only brings 100%atom economy but also addresses the challenge of stereoselective hydrotrifluoromethylation of aromatic alkynes.This unprecedented protocol offers an important access to a wide range of highly functionalized CF3-containing alkenes with great potential for post-modification.

关 键 词：氢三氟甲基化 可见光催化 原子经济性 氢转移 

分 类 号：O621.25[理学—有机化学]