Comins' reagent

The Comins' reagent is a triflyl-donating reagent that is used to synthesize vinyl triflates from the corresponding ketone enolates or dienolates.[1]

Sample Reaction With Comin's Reagent
Sample Reaction With Comin's Reagent
Comins' Reagent
Skeletal formula of Comin's Reagent
Names
Preferred IUPAC name
N-(5-Chloropyridin-2-yl)-N-(methanesulfonyl)methanesulfonamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.321
EC Number
  • 629-110-2
UNII
  • 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/h1-3H
    Key: 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/h1-3H
    Key: TUFGVZMNGTYAQD-UHFFFAOYAK
  • O=S(=O)(N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F)C(F)(F)F
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).
Infobox references

It was first reported in 1992 by Daniel Comins.[2] The vinyl triflates prepared are useful as substrates in the Suzuki reaction.[3]

See also

References
  1. Mundy, Bradford P.; Ellerd, Michael G.; Favaloro, Frank G., Jr. (2005). Name Reactions and Reagents in Organic Synthesis (2nd ed.). ISBN 978-0471228547.{{cite book}}: CS1 maint: multiple names: authors list (link)
  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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