Comins' reagent: Difference between revisions

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

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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.). 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.

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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.). 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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[2]

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@@ Line 3: / Line 3: @@
 | ImageFile = CominsReagent.png
 | ImageName = Skeletal formula of Comin's Reagent
+| ImageFile2 = Comin's reagent-3D-balls.png
-| IUPACName =
+| PIN = N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide
 |Section1={{Chembox Identifiers
 | CASNo = 145100-51-2
+| CASNo_Ref = {{Cascite|changed|CAS}}
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = WS933U9U66
+| EINECS = 629-110-2
 | PubChem = 388544
 | ChemSpiderID = 344376
@@ Line 26: / Line 31: @@
 }}
-'''Comins' reagent''' is a [[Trifluoromethylsulfonyl|triflyl]] compound 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 = 0471228540 | 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| publisher = John Wiley & Sons }}</ref>
 [[File:SampleReactionWithCominsReagent.png|center|500px|Sample Reaction With Comin's Reagent]]
-It was first reported in 1992 by Daniel Comins from North Carolina State University.<ref>{{cite journal | last = Comins | first = Daniel L. | last2 = Dehghani | first2 = Ali | title = Pyridine-Derived Triflating Reagents: An Improved Preparation of Vinyl Triflates from Metallo Enolates | journal = Tetrahedron Letters | year = 1992 | volume = 33 | issue = 42 | pages = 6299–6302 | doi = 10.1016/S0040-4039(00)60957-7}}</ref>  The vinyl triflates prepared are useful as substrates in the [[Suzuki reaction]].<ref>{{cite journal | last = Miyaura | first = Norio | last2 = Suzuki | first2 = Akira | title = Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds | journal = Chemical Reviews | year = 1995 | volume = 95 | pages = 2457–2483 | doi = 10.1021/cr00039a007 }}</ref>
+It was first reported in 1992 by Daniel Comins.<ref>{{cite journal | last1 = Comins | first1 = Daniel L. | last2 = Dehghani | first2 = Ali | title = Pyridine-Derived Triflating Reagents: An Improved Preparation of Vinyl Triflates from Metallo Enolates | journal = Tetrahedron Letters | year = 1992 | volume = 33 | issue = 42 | pages = 6299–6302 | doi = 10.1016/S0040-4039(00)60957-7}}</ref>  The vinyl triflates prepared are useful as substrates in the [[Suzuki reaction]].<ref>{{cite journal|author1-link=Norio Miyaura|author2-link=Akira Suzuki (chemist) | last1 = Miyaura | first1 = Norio | last2 = Suzuki | first2 = Akira | title = Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds | journal = Chemical Reviews | year = 1995 | volume = 95 | issue = 7 | pages = 2457–2483 | doi = 10.1021/cr00039a007 | citeseerx = 10.1.1.735.7660 }}</ref>
+==See also==
+* [[Bis(trifluoromethanesulfonyl)aniline]]
 ==References==
 {{Reflist}}
+[[Category:Reagents for organic chemistry]]
-==External links==
+[[Category:Chloropyridines]]
-* [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=24865208&viewopt=Deposited Comins' Reagent at PubChem]
+[[Category:Sulfonamides]]
+[[Category:Trifluoromethyl compounds]]
+[[Category:Substances discovered in the 1990s]]
+{{organic-compound-stub}}
-[[Category:Reagents for organic chemistry]]
-{{chem-stub}}