Starting from Styrene: A Unified Protocol for Hydrotrifluoromethylation of Diversified Alkenes

In contrast with unactivated alkenes, the corresponding hydrotrifluoromethylation of styrene has remained challenging due to the strong propensity of styrene for oligomerization and polymerization. On the basis of our newly developed trifluoromethylation reagent, TFSP, herein we present a general me...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 23; pp. 9277 - 9282
Main Authors Yang, Yi-Fei, Lin, Jin-Hong, Xiao, Ji-Chang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.12.2021
Amer Chemical Soc
Subjects
acrylamides
acrylates
alkenes
catalytic activity
Chemistry
Chemistry, Organic
oligomerization
Physical Sciences
polymerization
redox reactions
Science & Technology
styrene
DONOR-ACCEPTOR COMPLEX
CATALYTIC HYDROTRIFLUOROMETHYLATION
OXIDATION
REAGENT
3-COMPONENT OXYTRIFLUOROMETHYLATION
PHOTOREDOX
ORGANOSILANES
RADICAL TRIFLUOROMETHYLATION
EFFICIENT
UNACTIVATED ALKENES
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Summary:In contrast with unactivated alkenes, the corresponding hydrotrifluoromethylation of styrene has remained challenging due to the strong propensity of styrene for oligomerization and polymerization. On the basis of our newly developed trifluoromethylation reagent, TFSP, herein we present a general method for the hydrotrifluoromethylation of styrene under photoredox catalysis. The substrate scope was further extended to unactivated alkenes, acrylates, acrylamides, and vinyl-heteroatom-substituted alkenes. The tunability of this method was showcased via the relevant deprotonative trifluoromethylation and trifluoromethyltrifluoroethoxylation reactions.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c03630