Comins' reagent

Comins' Reagent
Names
	Preferred IUPAC name N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide
Identifiers
CAS Number	145100-51-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	344376;
ECHA InfoCard	100.157.321
EC Number	629-110-2;
PubChem CID	388544;
UNII	WS933U9U66 ;
CompTox Dashboard (EPA)	DTXSID40327763 ;
	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/h1-3H 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;
	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−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

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

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.

References

^ 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.
^ 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 (7): 2457–2483. CiteSeerX 10.1.1.735.7660. doi:10.1021/cr00039a007.
^ Chuang, Kangway V.; Xu, Chen; Reisman, Sarah E. (2016-08-26). "A 15-step synthesis of (+)-ryanodol". Science. 353 (6302): 912–915. doi:10.1126/science.aag1028. PMC 5505075. PMID 27563092.

[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. doi:10.1126/science.aag1028. PMC 5505075. PMID 27563092.

[1]

[2]

[3]

[4]

Mechanism

See also

References