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- W2898885539 endingPage "11748" @default.
- W2898885539 startingPage "11741" @default.
- W2898885539 abstract "Photoinduced, copper-catalyzed coupling reactions are emerging as a powerful method for generating Csp3–Y (Y = C or heteroatom) bonds from alkyl electrophiles and nucleophiles. Corresponding three-component couplings of alkyl electrophiles, olefins, and nucleophiles have the potential to generate an additional Csp3–Y bond and to efficiently add functional groups to both carbons of an olefin, which serves as a readily available linchpin. In this report, we establish that a variety of electrophiles and a trifluoromethylthiolate nucleophile can add across an array of olefins (including styrenes and electron-poor olefins) in the presence of CuI/binap and blue-LED irradiation, thereby generating trifluoromethyl thioethers in good yield. The process tolerates a wide range of functional groups, and an initial survey of other nucleophiles (i.e., bromide, cyanide, and azide) suggests that this three-component coupling strategy is versatile. Mechanistic studies are consistent with a photoexcited Cu(I)/binap/SCF3 complex serving as a reductant to generate an alkyl radical from the electrophile, which likely reacts in turn with the olefin and a Cu(II)/SCF3 complex to afford the coupling product." @default.
- W2898885539 created "2018-11-09" @default.
- W2898885539 creator A5016642366 @default.
- W2898885539 creator A5057055428 @default.
- W2898885539 creator A5071890036 @default.
- W2898885539 creator A5090735778 @default.
- W2898885539 date "2018-10-31" @default.
- W2898885539 modified "2023-10-18" @default.
- W2898885539 title "Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate To Generate Trifluoromethyl Thioethers" @default.
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