Copper-Catalyzed Synthesis of Thiadiazine-1-oxides in Reusable Aqueous Medium under External [Ag]/Ligand/Base-Free Conditions
We report herein a copper-catalyzed multicomponent reaction of simple NH-sulfoximine with readily available aldehyde and TMSN3 in hot water and aerobic conditions. The reaction tolerated a broad range of functional groups under external [Ag]/ligand/base-free conditions and can form three C-N bonds in a one-pot transformation, thus representing an extremely cost-effective protocol to biologically active sulfoximine derivatives. This aqueous catalytic system could be circularly utilized in consecutive runs of gram-scale preparations of thiadiazine-1-oxides without extra addition of the copper catalyst and PTA. Mechanistically, an ″ortho-binding″ effect in ortho-bromo NH-sulfoximine was proposed to control the chemoselectivity; thus, the other free halides such as bromo- or iodo-atoms in aldehydes 2 were compatible in the reaction.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:85 |
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| Enthalten in: |
The Journal of organic chemistry - 85(2020), 2 vom: 17. Jan., Seite 841-850 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Wu, Cui [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 04.03.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.joc.9b02828 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM304500380 |
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| 245 | 1 | 0 | |a Copper-Catalyzed Synthesis of Thiadiazine-1-oxides in Reusable Aqueous Medium under External [Ag]/Ligand/Base-Free Conditions |
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| 500 | |a Date Revised 04.03.2020 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a We report herein a copper-catalyzed multicomponent reaction of simple NH-sulfoximine with readily available aldehyde and TMSN3 in hot water and aerobic conditions. The reaction tolerated a broad range of functional groups under external [Ag]/ligand/base-free conditions and can form three C-N bonds in a one-pot transformation, thus representing an extremely cost-effective protocol to biologically active sulfoximine derivatives. This aqueous catalytic system could be circularly utilized in consecutive runs of gram-scale preparations of thiadiazine-1-oxides without extra addition of the copper catalyst and PTA. Mechanistically, an ″ortho-binding″ effect in ortho-bromo NH-sulfoximine was proposed to control the chemoselectivity; thus, the other free halides such as bromo- or iodo-atoms in aldehydes 2 were compatible in the reaction | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Huang, Riting |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Ming |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Zhiyuan |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t The Journal of organic chemistry |d 1945 |g 85(2020), 2 vom: 17. Jan., Seite 841-850 |w (DE-627)NLM000006343 |x 1520-6904 |7 nnns |
| 773 | 1 | 8 | |g volume:85 |g year:2020 |g number:2 |g day:17 |g month:01 |g pages:841-850 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.joc.9b02828 |3 Volltext |
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