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Comins' reagent

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Comins' Reagent
Skeletal formula of Comin's Reagent
Names
Preferred IUPAC name N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.321 Edit this at Wikidata
EC Number
  • 629-110-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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/h1-3HKey: TUFGVZMNGTYAQD-UHFFFAOYSA-N
  • 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/h1-3HKey: TUFGVZMNGTYAQD-UHFFFAOYAK
SMILES
  • O=S(=O)(N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F)C(F)(F)F
Properties
Chemical formula C7H3ClF6N2O4S2
Molar mass 392.67 g·mol
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 , 100 kPa). Infobox references
Chemical compound

The Comins' reagent is a triflyl-donating reagent that is used to synthesize vinyl triflates from the corresponding ketone enolates or dienolates.

Sample Reaction With Comin's Reagent
Sample Reaction With Comin's Reagent

It was first reported in 1992 by Daniel Comins. The vinyl triflates prepared are useful as substrates in the Suzuki reaction.

See also

References

  1. Mundy, Bradford P.; Ellerd, Michael G.; Favaloro, Frank G. Jr. (2005). Name Reactions and Reagents in Organic Synthesis (2nd ed.). John Wiley & Sons. ISBN 978-0471228547.
  2. 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.
  3. Miyaura, Norio; Suzuki, Akira (1995). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds". Chemical Reviews. 95 (7): 2457–2483. CiteSeerX 10.1.1.735.7660. doi:10.1021/cr00039a007.


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