5736-59-4Relevant academic research and scientific papers
Ni-promoted Cyclopentenone Formation by Intramolecular Cyclocarbonylation of 1-Bromo-1,4-dienes
Lleberia, Amadeu,Camps, Francisco,Moreto, Josep M.
, p. 1283 - 1296 (1993)
Stereoselective syn addition of allyl bromide to acetylenes catalysed by palladium(II) bromide results in the formation of 1-bromo-1,4-dienes which were further converted to cyclopentenones through a Ni(CO)4 promoted carbonylation-cyclization process.Four C-C bonds are formed by this two step sequence, leading to 2,3-substituted 5-methoxycarbonylmethylcyclopentenones 1.Application of this procedure to 2-butyne affords cyclopentenone 1c, an immediate precursor of the antibiotic methylenomycin B.
Palladium-catalyzed cyclopentenone formation by carbonylative cycloaddition of allylic tosylates and alkynes
Tsukada, Naofumi,Sugawara, Shuichi,Okuzawa, Tomohiro,Inoue, Yoshio
, p. 3003 - 3008 (2008/02/10)
Carbonylative cycloaddition of allyl tosylates and alkynes proceeded in the presence of palladium catalysts to afford a range of cyclopentenones. In the presence of methanol, five-component coupling reactions gave methyl cyclopentenyl acetates, whereas in the absence of methanol, (cyclopentenoylmethylidene)furanones were formed from six components. Allyl tosylate was found to be essential for these reactions, as allyl acetate and allyl bromide proved to be ineffective. Georg Thieme Verlag Stuttgart.
The Ni-mediated cyclocarbonylation of allyl halides and alkynes made catalytic. Evidence supporting the involvement of pseudoradical NiI species in the mechanism
Nadal, M. Lluisa,Bosch, Julia,Vila, Josep M.,Klein, Guenter,Ricart, Susagna,Moreto, Josep M.
, p. 10476 - 10477 (2007/10/03)
We report here on a highly efficient catalytic method to synthesize intermolecularly the cyclopentane skeleton from starting products as simple as allyl halides, alkynes, and carbon monoxide under very mild reaction conditions by means of a substoichiomet
A TWO STEP PROCEDURE AS IMPROVED ALTERNATIVE TO THE CYCLOCARBONYLATION OF ALLYL HALIDES AND ACETYLENE DERIVATIVES MEDIATED BY Ni(CO)4
Camps. F.,Coll, J.,Llebaria, A.,Moreto, J. M.
, p. 5811 - 5814 (2007/10/02)
The addition of allyl halides to acetylenic derivatives catalyzed by Pd(II) complexes, such as bis-acetonitrile palladium(II) bromide, followed by cyclocarbonylation of the resulting cis adducts with Ni(CO)4 in CH3CN containing precise amounts of CH3OH an
