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{{chembox
{{Chembox
| Name = Comins' Reagent
| Name = Comins' Reagent
| ImageFile = CominsReagent.png
| ImageFile = CominsReagent.png
| ImageName = Skeletal formula of Comin's Reagent
| ImageSize = 200px
| 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
| IUPACName =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 145100-51-2
| CASNo = 145100-51-2
| CASNo_Ref = {{Cascite|changed|CAS}}
| SMILES =
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem = 24865208
| UNII = WS933U9U66
⚫
}}
| EINECS = 629-110-2
⚫
| Section2 = {{Chembox Properties
⚫
| PubChem = 388544
⚫
| C = 7 | H = 3 | Cl = 1 | F = 6 | N = 2 | O = 4 | S = 2
| MeltingPtC = 45
| ChemSpiderID = 344376
| SMILES = O=S(=O)(N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F)C(F)(F)F
⚫
| BoilingPtC =
| 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
⚫
| Density =
| InChIKey = TUFGVZMNGTYAQD-UHFFFAOYAK
⚫
| FlashPt =
| 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
⚫
| Appearance = White solid
| 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 =
}}
}}
}}


'''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]]
[[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==
==References==
{{Reflist}}
{{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]]



{{chem-stub}}
{{organic-compound-stub}}

Latest revision as of 20:19, 2 December 2024

Comins' Reagent
Skeletal formula of Comin's Reagent
Names
Preferred IUPAC name
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.321 Edit this at Wikidata
EC Number
  • 629-110-2
UNII
  • 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
  • O=S(=O)(N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F)C(F)(F)F
Properties
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).

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

Sample Reaction With Comin's Reagent
Sample Reaction With Comin's Reagent

It was first reported in 1992 by Daniel Comins.[2] The vinyl triflates prepared are useful as substrates in the Suzuki reaction.[3]

See also

[edit]

References

[edit]
  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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