Vinyl Triflate Synthesis Essay

Related Content:

  • Total Synthesis of (−)-Himalensine A

    Journal of the American Chemical Society

    Shi, Michaelides, Darses, Jakubec, Nguyen, Paton, and Dixon

    2017139 (49), pp 17755–17758

    Abstract: The first enantioselective synthesis of (−)-himalensine A has been achieved in 22 steps. The synthesis was enabled by a novel catalytic, enantioselective prototropic shift/furan Diels–Alder (IMDAF) cascade to construct the ACD tricyclic core. A reductive ...

    Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

  • Vinyl triflates: a mechanistic study on their formation from carbonyl compounds and triflic anhydride

    The Journal of Organic Chemistry

    Wright, Pulley

    198954 (12), pp 2886–2889

    Abstract | Hi-Res PDF

  • NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist


    Fulmer, Miller, Sherden, Gottlieb, Nudelman, Stoltz, Bercaw and Goldberg

    201029 (9), pp 2176–2179

    Abstract: Tables of 1H and 13C NMR chemical shifts have been compiled for common organic compounds often used as reagents or found as products or contaminants in deuterated organic solvents. Building upon the work of Gottlieb, Kotlyar, and Nudelman in the Journal ...Tables of 1H and 13C NMR resonances for common organic contaminants are reported in 12 different deuterated organic solvents frequently used to study organometallic systems. This manuscript catalogs the chemical shifts for nearly 60 gases and organic compounds which are commonly used as reagents or internal standards or are found as products in organometallic reactions.

    Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

  • Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic Photoredox Catalysis

    Journal of the American Chemical Society

    Tay and Nicewicz

    2017139 (45), pp 16100–16104

    Abstract: Nucleophilic aromatic substitution (SNAr) is a direct method for arene functionalization; however, it can be hampered by low reactivity of arene substrates and their availability. Herein we describe a cation radical-accelerated nucleophilic aromatic ...

    Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

  • Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents

    The Journal of Organic Chemistry

    Batesky, Goldfogel, and Weix

    201782 (19), pp 9931–9936

    Abstract: While the use of triphenylphosphine as a reductant is common in organic synthesis, the resulting triphenylphosphine oxide (TPPO) waste can be difficult to separate from the reaction product. While a number of strategies to precipitate TPPO are available, ...

    Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

  • Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes

    Journal of the American Chemical Society

    Condakes, Hung, Harwood, and Maimone

    2017139 (49), pp 17783–17786

    Abstract: We report the first chemical syntheses of both (−)-majucin and (−)-jiadifenoxolane A via 10 net oxidations from the ubiquitous terpene (+)-cedrol. Additionally, this approach allows for access to other majucin-type sesquiterpenes, like (−)-jiadifenolide, (...

    Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

  • Names
    IUPAC name
    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
    • 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
    • O=S(=O)(N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F)C(F)(F)F
    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]


    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. 

    0 Replies to “Vinyl Triflate Synthesis Essay”

    Lascia un Commento

    L'indirizzo email non verrà pubblicato. I campi obbligatori sono contrassegnati *