Comins' reagent

Last updated
Comins' Reagent
Skeletal formula of Comin's Reagent Comins-Reagenz.svg
Skeletal formula of Comin's Reagent
Comin's reagent-3D-balls.png
Names
Preferred IUPAC name
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.321 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 629-110-2
PubChem CID
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
AppearanceWhite 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).

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

Contents

Sample Reaction With Comin's Reagent SampleReactionWithCominsReagent.png
Sample Reaction With Comin's Reagent

It was first reported in 1992 by Daniel Comins. [2] The vinyl triflates prepared are useful as substrates in the Suzuki reaction [3] or other cross-coupling reactions. [4]

Mechanism

First an enolate is created through deprotonation of the carbonyl compound. Then the nucleophilic oxygen will attack one of the sulfurs while the rest of Comins reagent will work as a leaving group due to the good charge stabilization.

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.
  4. ↑ Chuang, Kangway V.; Xu, Chen; Reisman, Sarah E. (2016-08-26). "A 15-step synthesis of (+)-ryanodol". Science. 353 (6302): 912–915. Bibcode:2016Sci...353..912C. doi:10.1126/science.aag1028. PMC   5505075 . PMID   27563092.


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