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- Publisher Website: 10.1021/acscatal.8b04094
- Scopus: eid_2-s2.0-85056738988
- WOS: WOS:000453491100075
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Article: Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers
Title | Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers |
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Authors | |
Keywords | copper catalysis C-S bond formation photochemistry photoredox catalysis three-component cross-coupling |
Issue Date | 2018 |
Citation | ACS Catalysis, 2018, v. 8, n. 12, p. 11741-11748 How to Cite? |
Abstract | © 2018 American Chemical Society. 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/SCF 3 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)/SCF 3 complex to afford the coupling product. |
Persistent Identifier | http://hdl.handle.net/10722/276617 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | He, Jian | - |
dc.contributor.author | Chen, Caiyou | - |
dc.contributor.author | Fu, Gregory C. | - |
dc.contributor.author | Peters, Jonas C. | - |
dc.date.accessioned | 2019-09-18T08:34:09Z | - |
dc.date.available | 2019-09-18T08:34:09Z | - |
dc.date.issued | 2018 | - |
dc.identifier.citation | ACS Catalysis, 2018, v. 8, n. 12, p. 11741-11748 | - |
dc.identifier.uri | http://hdl.handle.net/10722/276617 | - |
dc.description.abstract | © 2018 American Chemical Society. 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/SCF 3 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)/SCF 3 complex to afford the coupling product. | - |
dc.language | eng | - |
dc.relation.ispartof | ACS Catalysis | - |
dc.subject | copper catalysis | - |
dc.subject | C-S bond formation | - |
dc.subject | photochemistry | - |
dc.subject | photoredox catalysis | - |
dc.subject | three-component cross-coupling | - |
dc.title | Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/acscatal.8b04094 | - |
dc.identifier.scopus | eid_2-s2.0-85056738988 | - |
dc.identifier.volume | 8 | - |
dc.identifier.issue | 12 | - |
dc.identifier.spage | 11741 | - |
dc.identifier.epage | 11748 | - |
dc.identifier.eissn | 2155-5435 | - |
dc.identifier.isi | WOS:000453491100075 | - |
dc.identifier.issnl | 2155-5435 | - |