DC Field | Value | Language |
---|---|---|
dc.contributor.author | Choi, Wonjun | ko |
dc.contributor.author | Kim, Leejae | ko |
dc.contributor.author | Hong, Sungwoo | ko |
dc.date.accessioned | 2024-09-12T06:00:06Z | - |
dc.date.available | 2024-09-12T06:00:06Z | - |
dc.date.created | 2024-09-12 | - |
dc.date.issued | 2024-05 | - |
dc.identifier.citation | ADVANCED SCIENCE, v.11, no.19 | - |
dc.identifier.uri | http://hdl.handle.net/10203/322938 | - |
dc.description.abstract | Despite the simplicity and abundance of ethylene, its practical application presents significant hurdles due to its nature as a highly flammable gas. Herein, a strategic use of easily handled vinyl ether is reported as a latent ethylene surrogate achieved via a spin-center shift (SCS) pathway, enabling the successful three-component reaction that bridges heteroarenes and various coupling partners, including sulfinates, thiols, and phosphine oxides. Through a photoredox catalytic process, alpha-oxy radicals are generated by combining various radicals with phenyl vinyl ether, which are subsequently added to N-heteroarenes. Subsequently, the radical-mediated SCS pathway serves as the driving force for CO bond cleavage, effectively engaging the phenoxy group as a leaving group. In addition, by broadening the utility of the method, a valuable synthon is provided for efficient CH vinylation of N-heteroarenes following sulfonyl group elimination. This approach not only enriches the toolbox of synthetic methodology but also provides a more streamlined alternative, circumventing the challenges associated with direct ethylene gas usage. The versatility of the method, particularly evident in late-stage functionalizations of medicinally relevant molecules and peptides, underscores its capability to produce invaluable three-component compounds and vinylated N-heteroarene derivatives. | - |
dc.language | English | - |
dc.publisher | WILEY | - |
dc.title | Unraveling the Potential of Vinyl Ether as an Ethylene Surrogate in Heteroarene C―H Functionalization via the Spin-Center Shift | - |
dc.type | Article | - |
dc.identifier.wosid | 001183798300001 | - |
dc.identifier.scopusid | 2-s2.0-85187496101 | - |
dc.type.rims | ART | - |
dc.citation.volume | 11 | - |
dc.citation.issue | 19 | - |
dc.citation.publicationname | ADVANCED SCIENCE | - |
dc.identifier.doi | 10.1002/advs.202309800 | - |
dc.contributor.localauthor | Hong, Sungwoo | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | CH vinylation | - |
dc.subject.keywordAuthor | ethylene surrogate | - |
dc.subject.keywordAuthor | spin-center shift (SCS) | - |
dc.subject.keywordAuthor | vinyl ether | - |
dc.subject.keywordAuthor | alpha-oxy radical | - |
dc.subject.keywordPlus | METAL-FREE | - |
dc.subject.keywordPlus | RADICALS | - |
dc.subject.keywordPlus | TETRAFLUOROETHYLENE | - |
dc.subject.keywordPlus | DIFUNCTIONALIZATION | - |
dc.subject.keywordPlus | GENERATION | - |
dc.subject.keywordPlus | ALDEHYDES | - |
dc.subject.keywordPlus | ALKENES | - |
dc.subject.keywordPlus | KETONES | - |
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