109123-22-0Relevant articles and documents
NHC-Mediated Synthesis of Tricyclic Spirocarbocycles via an Intramolecular Stetter Reaction of Cyclic Enal-Enones
Hsu, Day-Shin,Liang, Suz-Ping
, p. 1270 - 1278 (2020)
A general and efficient method for the synthesis of tricyclic spirocarbocycles is described. Various cyclic enal-enones were reacted with an N-heterocyclic carbene, and an intramolecular Stetter reaction proceeded smoothly to give various tricyclic spiro-
Palladium-catalyzed carbonylative cyclization of unsaturated aryl iodides and dienyl triflates, iodides, and bromides to indanones and 2-cyclopentenones
Gagnier, Steve V.,Larock, Richard C.
, p. 4804 - 4807 (2007/10/03)
Indanones and 2-cyclopentenones have been successfully prepared in good to excellent yields by the palladium-catalyzed carbonylative cyclization of unsaturated aryl iodides and dienyl triflates, iodides, and bromides, respectively. The best results are obtained by employing 10 mol % of Pd(OAc)2, 2 equiv of pyridine, 1 equiv of n-Bu4NCl, 1 atm of CO, a reaction temperature of 100 °C, and DMF as the solvent. This carbonylative cyclization is particularly effective on substrates that contain a terminal olefin. The proposed mechanism for this annulation includes (1) Pd(OAc)2 reduction to the active palladium(0) catalyst, (2) oxidative addition of the organic halide or triflate to Pd(0), (3) coordination and insertion of carbon monoxide to produce an acylpalladium intermediate, (4) acylpalladation of the neighboring carbon-carbon double bond, (5) reversible palladium β-hydride elimination and re-addition to form a palladium enolate, and (6) protonation by H2O to produce the indanone or 2-cyclopentenone.
Ambifunctional Reactivity of 3-Trifloxypropeniminium Salts Towards Nucleophiles
Singer, Berndt,Maas, Gerhard
, p. 1683 - 1690 (2007/10/02)
Reaction of 3-trifloxypropeniminium salts 1 with nucleophiles may occur at carbon atoms C-1 or C-3.Hydrolysis of 1a-e leads to β-formylvinyl triflates 2 preferentially.The trifloxy group at C-3 is substituted in most cases by sulfur or nitrogen nucleophil
