Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp3)-H Functionalization

doi:10.6023/cjoc201901021

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1613-1622.DOI: 10.6023/cjoc201901021 Previous Articles Next Articles

Special Issue: 碳氢活化合辑2018-2019

Articles

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(sp³)-H键官能团化

刘涛^a, 屈川华^a, 谢劲^a, 朱成建^a,b

a 南京大学化学化工学院南京 210023;
b 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

收稿日期:2019-01-16 修回日期:2019-01-24 发布日期:2019-02-19
通讯作者: 谢劲, 朱成建 E-mail:xie@nju.edu.cn;cjzhu@nju.edu.cn
基金资助:
国家自然科学基金（Nos.21702098，21732003，21672099）、青年千人资助项目和和本科有机化学实验课程开放课题资助项目.

Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp³)-H Functionalization

Liu Tao^a, Qu Chuanhua^a, Xie Jin^a, Zhu Chengjian^a,b

a School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032

Received:2019-01-16 Revised:2019-01-24 Published:2019-02-19
Contact: 10.6023/cjoc201901021 E-mail:xie@nju.edu.cn;cjzhu@nju.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21702098, 21732003, 21672099), the 1000-Youth Talents Plan and the Open Training Program of Undergraduate Organic Experiment Course.

1. Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp³)-H Functionalization.PDF(11525KB)

Abstract

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 of α-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.

Key words: hydrotrifluoromethylation, visible light, atom-economical, hydrogen transfer

Cite this article

Liu Tao, Qu Chuanhua, Xie Jin, Zhu Chengjian. Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp³)-H Functionalization[J]. Chin. J. Org. Chem., 2019, 39(6): 1613-1622.

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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(sp³)-H键官能团化

Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp³)-H Functionalization

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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(sp3)-H键官能团化