2021
DOI: 10.1021/acs.orglett.1c03630
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Starting from Styrene: A Unified Protocol for Hydrotrifluoromethylation of Diversified Alkenes

Abstract: 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-heteroatomsubstituted alkenes. The tun… Show more

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Cited by 38 publications
(16 citation statements)
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“…N ‐(3,3,3‐Trifluoropropyl)benzamide (2 b{β,3}) : [44] Yield 490 mg (85 %) from 2 a{β,3} ⋅HCl (400 mg, 2.67 mmol). White solid, m.p.=99–101 °C (lit.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…N ‐(3,3,3‐Trifluoropropyl)benzamide (2 b{β,3}) : [44] Yield 490 mg (85 %) from 2 a{β,3} ⋅HCl (400 mg, 2.67 mmol). White solid, m.p.=99–101 °C (lit.…”
Section: Methodsmentioning
confidence: 99%
“…96-97 °C). [44] 1 H NMR (400 MHz, CDCl 3 ): δ = 7.75 (d, J = 7.3 Hz, 2H), 7.51 (t, J = 7.3 Hz, 1H), 7.43 (t, J = 7.5 Hz, 2H), 6.56 (br s, 1H), 3.71 (q, J = 6.4 Hz, 2H), 2.46 ppm (qt, J = 10.8, 6.4 Hz, 2H). 13 C NMR (126 MHz, CDCl 3 ): δ = 167.9, 134.1, 131.9, 128.8, 127.0, 126.7 (q, J = 276.9 Hz), 33.8 (q, J = 27.7 Hz), 33.7 ppm (q, J = 3.8 Hz).…”
Section: N-(333-trifluoropropyl)benzamide (2 B{β3}mentioning
confidence: 99%
“…Also, they demonstrated the deprotonative trifluoromethylation to access C(sp 3 )-CF 3 bonds (Scheme 76: Condition C and Condition D). 145 5.2.2 C(sp 2 )-CF 3 bond formation. In 2019, Cook's group disclosed a photomediated strategy for 1,2-(bis)trifluoromethylation of (hetero)aryl acetylenes (Scheme 77).…”
Section: Photomediated Transformations For C-cf 3 Bond Formationmentioning
confidence: 99%
“…Also, they demonstrated the deprotonative trifluoromethylation to access C(sp 3 )–CF 3 bonds (Scheme 76: Condition C and Condition D). 145…”
Section: Photomediated Transformations For C–cf3 Bond Formationmentioning
confidence: 99%
“…Previously, we have described that the trifluoromethylsulfonyl-pyridinium salt TFSP, a white solid synthesized from Tf 2 O, is air-stable and convenient to use. 13 We have also realized an efficient azido or cyano-trifluoromethylation of alkenes employing TFSP as a facile CF 3 source. 14 Herein, we reported the visible light mediated C–H trifluoromethylation of unactivated (hetero)arenes in the presence of Ir(ppy) 3 under blue LED irradiation.…”
Section: Introductionmentioning
confidence: 99%