Comins' reagent

{{Chembox

| Name = Comins' Reagent

| ImageFile = Comin-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.{{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 }}

File:SampleReactionWithCominsReagent.png

It was first reported in 1992 by Daniel Comins.{{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}} The vinyl triflates prepared are useful as substrates in the Suzuki reaction{{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 }} or other cross-coupling reactions{{Cite journal |last=Chuang |first=Kangway V. |last2=Xu |first2=Chen |last3=Reisman |first3=Sarah E. |date=2016-08-26 |title=A 15-step synthesis of (+)-ryanodol |url=https://www.science.org/doi/10.1126/science.aag1028 |journal=Science |volume=353 |issue=6302 |pages=912–915 |doi=10.1126/science.aag1028 |pmc=5505075 |pmid=27563092}}.