期刊
ACS CATALYSIS
卷 8, 期 12, 页码 11741-11748出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b04094
关键词
copper catalysis; C-S bond formation; three-component cross-coupling; photoredox catalysis; photochemistry
资金
- National Institutes of Health (National Institute of General Medical Sciences) [R01-109194]
- Dow Next Generation Educator Fund [NSF-1531940]
Photoinduced, copper-catalyzed coupling reactions are emerging as a powerful method for generating Csp(3)-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 Csp(3)-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.
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