Unconventional reactivity of ethynylbenziodoxolone reagents and thiols: scope and mechanism
1,2-Dithio-1-alkenes are biologically active compounds widely implemented throughout organic synthesis, functional materials, coordination chemistry, and pharmaceuticals. Traditional methods for accessing 1,2-dithio-1-alkenes often demand transition metal catalysts, specialized or air-sensitive liga...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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Wiley
2020
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| _version_ | 1826292238522515456 |
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| author | Liu, B Alegre-Requena, JV Paton, RS Miyake, GM |
| author_facet | Liu, B Alegre-Requena, JV Paton, RS Miyake, GM |
| author_sort | Liu, B |
| collection | OXFORD |
| description | 1,2-Dithio-1-alkenes are biologically active compounds widely implemented throughout organic synthesis, functional materials, coordination chemistry, and pharmaceuticals. Traditional methods for accessing 1,2-dithio-1-alkenes often demand transition metal catalysts, specialized or air-sensitive ligands, high temperatures, and disulfides (R2 S2 ). Herein, a general and efficient strategy utilizing ethynylbenziodoxolone (EBX) reagents and thiols is presented that results in the formation of 1,2-dithio-1-alkenes with excellent regioselectivity and stereoselectivity through unprecedented reactivity between the EBX and the thiol. This operationally simple procedure utilizes mild conditions, which result in a broad substrate scope and high functional-group tolerance. The observed unexpected reactivity has been rationalized through both experimental results and DFT calculations. |
| first_indexed | 2024-03-07T03:11:36Z |
| format | Journal article |
| id | oxford-uuid:b463114f-8670-4403-8b40-1c5e7f1b8b31 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:11:36Z |
| publishDate | 2020 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:b463114f-8670-4403-8b40-1c5e7f1b8b312022-03-27T04:25:46ZUnconventional reactivity of ethynylbenziodoxolone reagents and thiols: scope and mechanismJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:b463114f-8670-4403-8b40-1c5e7f1b8b31EnglishSymplectic ElementsWiley2020Liu, BAlegre-Requena, JVPaton, RSMiyake, GM1,2-Dithio-1-alkenes are biologically active compounds widely implemented throughout organic synthesis, functional materials, coordination chemistry, and pharmaceuticals. Traditional methods for accessing 1,2-dithio-1-alkenes often demand transition metal catalysts, specialized or air-sensitive ligands, high temperatures, and disulfides (R2 S2 ). Herein, a general and efficient strategy utilizing ethynylbenziodoxolone (EBX) reagents and thiols is presented that results in the formation of 1,2-dithio-1-alkenes with excellent regioselectivity and stereoselectivity through unprecedented reactivity between the EBX and the thiol. This operationally simple procedure utilizes mild conditions, which result in a broad substrate scope and high functional-group tolerance. The observed unexpected reactivity has been rationalized through both experimental results and DFT calculations. |
| spellingShingle | Liu, B Alegre-Requena, JV Paton, RS Miyake, GM Unconventional reactivity of ethynylbenziodoxolone reagents and thiols: scope and mechanism |
| title | Unconventional reactivity of ethynylbenziodoxolone reagents and thiols: scope and mechanism |
| title_full | Unconventional reactivity of ethynylbenziodoxolone reagents and thiols: scope and mechanism |
| title_fullStr | Unconventional reactivity of ethynylbenziodoxolone reagents and thiols: scope and mechanism |
| title_full_unstemmed | Unconventional reactivity of ethynylbenziodoxolone reagents and thiols: scope and mechanism |
| title_short | Unconventional reactivity of ethynylbenziodoxolone reagents and thiols: scope and mechanism |
| title_sort | unconventional reactivity of ethynylbenziodoxolone reagents and thiols scope and mechanism |
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