One-pot sulfoxide synthesis exploiting a sulfinyl-dication equivalent generated from a DABSO/Trimethylsilyl Chloride sequence
A one-pot process for the synthesis of unsymmetrical sulfoxides using organometallic nucleophiles is described. Sulfur dioxide, delivered from the surrogate DABSO (DABCO-bis(sulfur dioxide)), acts as the initial electrophile and combines with the first organometallic reagent to generate a sulfinate...
| Main Authors: | , , , , |
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| Format: | Journal article |
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American Chemical Society
2016
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| _version_ | 1797092382898913280 |
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| author | Willis, M Lenstra, D Vedovato, V Flegeau, E Maydom, J |
| author_facet | Willis, M Lenstra, D Vedovato, V Flegeau, E Maydom, J |
| author_sort | Willis, M |
| collection | OXFORD |
| description | A one-pot process for the synthesis of unsymmetrical sulfoxides using organometallic nucleophiles is described. Sulfur dioxide, delivered from the surrogate DABSO (DABCO-bis(sulfur dioxide)), acts as the initial electrophile and combines with the first organometallic reagent to generate a sulfinate intermediate. In situ conversion of the sulfinate to a sulfinate silyl ester, using TMS-Cl (trimethylsilyl chloride), generates a second electrophile, allowing addition of a second organometallic reagent. Organolithium or Grignard reagents can be employed, delivering sulfoxides in good to excellent yields. |
| first_indexed | 2024-03-07T03:45:12Z |
| format | Journal article |
| id | oxford-uuid:bf3dc985-4e7d-4efb-a562-ce3728ba68e3 |
| institution | University of Oxford |
| last_indexed | 2024-03-07T03:45:12Z |
| publishDate | 2016 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:bf3dc985-4e7d-4efb-a562-ce3728ba68e32022-03-27T05:45:53ZOne-pot sulfoxide synthesis exploiting a sulfinyl-dication equivalent generated from a DABSO/Trimethylsilyl Chloride sequenceJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:bf3dc985-4e7d-4efb-a562-ce3728ba68e3Symplectic Elements at OxfordAmerican Chemical Society2016Willis, MLenstra, DVedovato, VFlegeau, EMaydom, JA one-pot process for the synthesis of unsymmetrical sulfoxides using organometallic nucleophiles is described. Sulfur dioxide, delivered from the surrogate DABSO (DABCO-bis(sulfur dioxide)), acts as the initial electrophile and combines with the first organometallic reagent to generate a sulfinate intermediate. In situ conversion of the sulfinate to a sulfinate silyl ester, using TMS-Cl (trimethylsilyl chloride), generates a second electrophile, allowing addition of a second organometallic reagent. Organolithium or Grignard reagents can be employed, delivering sulfoxides in good to excellent yields. |
| spellingShingle | Willis, M Lenstra, D Vedovato, V Flegeau, E Maydom, J One-pot sulfoxide synthesis exploiting a sulfinyl-dication equivalent generated from a DABSO/Trimethylsilyl Chloride sequence |
| title | One-pot sulfoxide synthesis exploiting a sulfinyl-dication equivalent generated from a DABSO/Trimethylsilyl Chloride sequence |
| title_full | One-pot sulfoxide synthesis exploiting a sulfinyl-dication equivalent generated from a DABSO/Trimethylsilyl Chloride sequence |
| title_fullStr | One-pot sulfoxide synthesis exploiting a sulfinyl-dication equivalent generated from a DABSO/Trimethylsilyl Chloride sequence |
| title_full_unstemmed | One-pot sulfoxide synthesis exploiting a sulfinyl-dication equivalent generated from a DABSO/Trimethylsilyl Chloride sequence |
| title_short | One-pot sulfoxide synthesis exploiting a sulfinyl-dication equivalent generated from a DABSO/Trimethylsilyl Chloride sequence |
| title_sort | one pot sulfoxide synthesis exploiting a sulfinyl dication equivalent generated from a dabso trimethylsilyl chloride sequence |
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