DC Field | Value | Language |
---|---|---|
dc.contributor.author | Kim, Jungwon | ko |
dc.contributor.author | Kang, Byungjoon | ko |
dc.contributor.author | Hong, Soon Hyeok | ko |
dc.date.accessioned | 2020-07-02T08:20:05Z | - |
dc.date.available | 2020-07-02T08:20:05Z | - |
dc.date.created | 2020-06-29 | - |
dc.date.created | 2020-06-29 | - |
dc.date.created | 2020-06-29 | - |
dc.date.issued | 2020-06 | - |
dc.identifier.citation | ACS CATALYSIS, v.10, no.11, pp.6013 - 6022 | - |
dc.identifier.issn | 2155-5435 | - |
dc.identifier.uri | http://hdl.handle.net/10203/275139 | - |
dc.description.abstract | In spite of the wide utility of allyl thioethers, the direct catalytic allylic C(sp(3))-H thiolation remains elusive. Herein, we report the direct allylic C(sp(3))-H thiolation mediated by visible light photoredox catalysis. The use of in situ-generated thiyl radical from disulfide as a hydrogen atom transfer (HAT) reagent and a coupling partner enabled selective cleavage of the allylic C(sp(3))-H bond followed by C(sp(3))-S bond formation. The undesired hydrothiolation, a prevalent reaction from facile thiyl radical addition to olefins, was prevented by the immediate deprotonation of thiol under basic conditions. A wide range of diaryl disulfides and olefins participated in the reaction, producing allyl thioethers with high efficiency. Mechanistic investigations revealed the participation of the photocatalyst as a redox mediator, which was crucial for the transformation of the allyl radical into the allyl cation and further ionic coupling process. Based on the proposed mechanism, a limitation in the synthesis of alkyl allyl sulfide was solved with a rationally designed more reducible unsymmetrical disulfide, which makes the desired catalytic cycle operative. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Direct Allylic C(sp(3))-H Thiolation with Disulfides via Visible Light Photoredox Catalysis | - |
dc.type | Article | - |
dc.identifier.wosid | 000538766900007 | - |
dc.identifier.scopusid | 2-s2.0-85086893610 | - |
dc.type.rims | ART | - |
dc.citation.volume | 10 | - |
dc.citation.issue | 11 | - |
dc.citation.beginningpage | 6013 | - |
dc.citation.endingpage | 6022 | - |
dc.citation.publicationname | ACS CATALYSIS | - |
dc.identifier.doi | 10.1021/acscatal.0c01232 | - |
dc.contributor.localauthor | Hong, Soon Hyeok | - |
dc.contributor.nonIdAuthor | Kim, Jungwon | - |
dc.contributor.nonIdAuthor | Kang, Byungjoon | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | C-H activation | - |
dc.subject.keywordAuthor | allylic compound | - |
dc.subject.keywordAuthor | allyl thioether | - |
dc.subject.keywordAuthor | photocatalysis | - |
dc.subject.keywordAuthor | C-S bond formation | - |
dc.subject.keywordPlus | SP(3) C-H | - |
dc.subject.keywordPlus | SELECTIVE AEROBIC OXIDATION | - |
dc.subject.keywordPlus | ENE REACTIONS | - |
dc.subject.keywordPlus | ASYMMETRIC-SYNTHESIS | - |
dc.subject.keywordPlus | HIGHLY EFFICIENT | - |
dc.subject.keywordPlus | DIALLYL SULFIDE | - |
dc.subject.keywordPlus | METAL-FREE | - |
dc.subject.keywordPlus | C=C BONDS | - |
dc.subject.keywordPlus | ALLYLATION | - |
dc.subject.keywordPlus | ALKYLATION | - |
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