Comins' reagent: Difference between revisions
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| CASNo = 145100-51-2 |
| CASNo = 145100-51-2 |
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| SMILES = |
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| PubChem = 388544 |
| PubChem = 388544 |
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| PubChem = 388544 |
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| ChemSpiderID = 344376 |
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| SMILES = O=S(=O)(N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F)C(F)(F)F |
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| InChI = 1/C7H3ClF6N2O4S2/c8-4-1-2-5(15-3-4)16(21(17,18)6(9,10)11)22(19,20)7(12,13)14/h1-3H |
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| InChIKey = TUFGVZMNGTYAQD-UHFFFAOYAK |
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| StdInChI = 1S/C7H3ClF6N2O4S2/c8-4-1-2-5(15-3-4)16(21(17,18)6(9,10)11)22(19,20)7(12,13)14/h1-3H |
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| StdInChIKey = TUFGVZMNGTYAQD-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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Revision as of 15:31, 14 October 2012
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| Identifiers | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.157.321 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C7H3ClF6N2O4S2 | |
| Molar mass | 392.67 g·mol−1 |
| Appearance | White solid |
| Melting point | 45 °C (113 °F; 318 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Comins' reagent is a triflyl compound that is used to synthesize vinyl triflates from the corresponding ketone enolates or dienolates.[1]
It was first reported in 1992 by Daniel Comins from North Carolina State University.[2] The vinyl triflates prepared are useful as substrates in the Suzuki reaction.[3]
References
- ^ Mundy, Bradford P.; Ellerd, Michael G.; Favaloro, Frank G., Jr. (2005). Name Reactions and Reagents in Organic Synthesis (2nd ed.). ISBN 0471228540.
{{cite book}}: CS1 maint: multiple names: authors list (link) - ^ Comins, Daniel L.; Dehghani, Ali (1992). "Pyridine-Derived Triflating Reagents: An Improved Preparation of Vinyl Triflates from Metallo Enolates". Tetrahedron Letters. 33 (42): 6299–6302. doi:10.1016/S0040-4039(00)60957-7.
- ^ Miyaura, Norio; Suzuki, Akira (1995). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds". Chemical Reviews. 95: 2457–2483. doi:10.1021/cr00039a007.
External links
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