COMMUNICATIONS
DOI: 10.1002/adsc.202001434
Visible-Light-Induced Three-Component Intermolecular
Trifluoromethyl-Alkenylation Reactions of Unactivated Alkenes
Yuan-Qiang Guo,a Kaihua Wang,a Ruiguo Wang,a Hongjian Song,a Yuxiu Liu,a
a
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry,
Nankai University, Tianjin 300071, People’s Republic of China
E-mail: wangqm@nankai.edu.cn
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, People’s Republic of China
b
Manuscript received: November 17, 2020; Revised manuscript received: January 4, 2021;
Version of record online: Februar 4, 2021
Dedicated to the 100th anniversary of Chemistry at Nankai University.
cluding transition-metal-catalyzed reactions, visible-
light-mediated reactions, reactions involving both
Abstract: Herein, we describe a practical protocol
for efficient, mild, visible-light-induced three-com-
photoredox and transition-metal catalysts, and electro-
ponent intermolecular trifluoromethyl-alkenylation
catalytic fluoroalkylation reactions.[4] Of these meth-
reactions of unactivated alkenes. The protocol has
ods, one of the most attractive involves difunctionali-
good functional group tolerance and a broad
zation of alkenes with CF3 radical (such as the
substrate scope. Using this protocol, we not only
Umemoto reagent,[5] Togni reagents,[6] Langlois’
introduced a trifluoromethyl group into alkenes but
also converted unactivated alkenes to styrene-based
reagent,[7] CF3SO2Cl,[8] CF3I,[9] CF3Br,[10] TMSCF3,[11]
CF3SO2NHNHBoc,[12] (CF3CO)2O[13] and (bpy)
activated alkenes, in addition to accomplishing late-
Cu(CF3)3[14]) (Scheme 1A). Using these reagents, many
stage functionalization of pharmaceutical intermedi-
research groups have achieved various difunctional
ates.
modifications of the styrenes and unactivated alkenes
through trifluoromethyl radicals. These research results
can be divided into carbo-CF3,[15] amino-CF3,[16] oxo-
Keywords: Photocatalysis; Three components; Un-
activated alkenes; Trifluoromethylation; Alkenylation
CF3,[17] thio-CF3,[18] halo-CF3.[19] and so on.
In the past few decades, considerable progress has
been made in the development of methods capable of
synthesizing CF3-containing molecules, with particular
The development of fluorine chemistry has great emphasis on the direct trifluoromethylation of alkenes.
significance for organic synthesis because introduction These remarkable achievements can help us effectively
of a fluorine atom or fluorinated moiety into a
molecule can improve its physical, chemical, or bio-
logical properties.[1] For example, replacing a hydrogen
atom or methyl group with a trifluoromethyl group
(CF3) markedly alters a molecule’s lipophilicity,
absorbability, metabolic stability, hydrophobicity, and
binding selectivity.[2]
Intermolecular difunctionalization of alkenes, a
transformation that forms two chemical bonds in a
single reaction, is an efficient, atom-economical
method for constructing complex organic molecules
from inexpensive, readily available starting materials.[3]
Over the past few decades, a number of methods for
alkene difunctionalization have been developed, in-
Scheme 1. Trifluoromethylative difunctionalization of alkenes.
Adv. Synth. Catal. 2021, 363, 1651–1655
1651
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