{{Chembox | Name = Comins' Reagent | ImageFile = Comins-Reagenz.svg | ImageName = Skeletal formula of Comin's Reagent | ImageFile2 = Comin's reagent-3D-balls.png | 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 | SMILES = O=S(=O)(N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F)C(F)(F)F | 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 | InChIKey = TUFGVZMNGTYAQD-UHFFFAOYAK | StdInChI = 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 | StdInChIKey = TUFGVZMNGTYAQD-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=7 | H=3 | Cl=1 | F=6 | N=2 | O=4 | S=2 | Appearance = White solid | MeltingPtC = 45 | BoilingPtC = | Density = }} |Section7={{Chembox Hazards | FlashPt = }} }}
The '''Comins' reagent''' is a triflyl-donating reagent that is used to synthesize vinyl 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>
center|500px|Sample Reaction With Comin's Reagent
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> or other cross-coupling reactions.<ref>{{Cite journal |last1=Chuang |first1=Kangway V. |last2=Xu |first2=Chen |last3=Reisman |first3=Sarah E. |date=2016-08-26 |title=A 15-step synthesis of (+)-ryanodol |journal=Science |volume=353 |issue=6302 |pages=912–915 |doi=10.1126/science.aag1028 |pmc=5505075 |pmid=27563092 |bibcode=2016Sci...353..912C }}</ref>
== 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== * Bis(trifluoromethanesulfonyl)aniline
==References== {{Reflist}}
Category:Reagents for organic chemistry Category:Chloropyridines Category:Sulfonamides Category:Trifluoromethyl compounds Category:Substances discovered in the 1990s Category:Disubstituted pyridines