Vinyl Triflate Synthesis Essay

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  • Names
    IUPAC name
    N,N-Bis(trifluoromethylsulfonyl)-5-chloro-2-pyridylamine
    Identifiers
    ChemSpider
    ECHA InfoCard100.157.321
    • 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 mass392.67 g·mol−1
    AppearanceWhite solid
    Melting point45 °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

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

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

    References[edit]

    1. ^Mundy, Bradford P.; Ellerd, Michael G.; Favaloro, Frank G., Jr. (2005). Name Reactions and Reagents in Organic Synthesis (2nd ed.). ISBN 0471228540. 
    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: 2457–2483. doi:10.1021/cr00039a007. 

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