Citation: Liu Tao, Qu Chuanhua, Xie Jin, Zhu Chengjian. Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp³)-H Functionalization[J]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1613-1622. doi: 10.6023/cjoc201901021 shu

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

Corresponding author: Xie Jin, xie@nju.edu.cn Zhu Chengjian, cjzhu@nju.edu.cn
Received Date: 16 January 2019
Revised Date: 24 January 2019
Available Online: 19 June 2019
Fund Project: 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 Coursethe National Natural Science Foundation of China 21732003the National Natural Science Foundation of China 21702098the National Natural Science Foundation of China 21672099

Figures(4)

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.
- hydrotrifluoromethylation,
- visible light,
- atom-economical,
- hydrogen transfer
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Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp3)-H Functionalization

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通讯作者: 陈斌, bchen63@163.com

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