Comins' reagent: Difference between revisions

Comins' Reagent
Names
	Preferred IUPAC name N-(5-Chloropyridin-2-yl)-N-(methanesulfonyl)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

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Revision as of 20:08, 27 March 2024

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]

References

^ Mundy, Bradford P.; Ellerd, Michael G.; Favaloro, Frank G. Jr. (2005). Name Reactions and Reagents in Organic Synthesis (2nd ed.). 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.

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[1] Mundy, Bradford P.; Ellerd, Michael G.; Favaloro, Frank G. Jr. (2005). Name Reactions and Reagents in Organic Synthesis (2nd ed.). 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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 }}
-The '''Comins' reagent''' is a [[Trifluoromethylsulfonyl|triflyl]]-donating reagent that is used to synthesize vinyl [[Trifluoromethanesulfonate|triflates]] from the corresponding ketone enolates or dienolates.<ref>{{cite book | last1 = Mundy | first1 = Bradford P. | last2 = Ellerd | first2 = Michael G. | last3 = Favaloro | first3 = Frank G., Jr. | title = Name Reactions and Reagents in Organic Synthesis | isbn = 978-0471228547 | edition = 2nd | year = 2005}}</ref>
+The '''Comins' reagent''' is a [[Trifluoromethylsulfonyl|triflyl]]-donating reagent that is used to synthesize vinyl [[Trifluoromethanesulfonate|triflates]] from the corresponding ketone enolates or dienolates.<ref>{{cite book | last1 = Mundy | first1 = Bradford P. | last2 = Ellerd | first2 = Michael G. | last3 = Favaloro | first3 = Frank G. Jr. | title = Name Reactions and Reagents in Organic Synthesis | isbn = 978-0471228547 | edition = 2nd | year = 2005}}</ref>
 [[File:SampleReactionWithCominsReagent.png|center|500px|Sample Reaction With Comin's Reagent]]
@@ Line 48: / Line 48: @@
 [[Category:Trifluoromethyl compounds]]
 [[Category:Substances discovered in the 1990s]]
 {{organic-compound-stub}}

Revision as of 20:08, 27 March 2024

See also

References