1355323-10-2Relevant academic research and scientific papers
Palladium-catalyzed synthesis of terminal acetals via highly selective anti-Markovnikov nucleophilic attack of pinacol on vinylarenes, allyl ethers, and 1,5-dienes
Yamamoto, Mayumi,Nakaoka, Sonoe,Ura, Yasuyuki,Kataoka, Yasutaka
, p. 1165 - 1167 (2012)
A palladium-catalyzed reaction of vinylarenes, allyl ethers, and 1,5-dienes with pinacol proceeded via a selective anti-Markovnikov nucleophilic attack to afford corresponding terminal acetals as major products. The bulkiness of pinacol was found to be critical in controlling the regioselectivity. The Royal Society of Chemistry 2012.
Palladium-catalyzed anti-Markovnikov oxidative acetalization of activated olefins with iron(iii) sulphate as the reoxidant
Fernandes, Rodney A.,Kumar, Praveen,Yadav, Sandhya S.
, p. 427 - 443 (2022/01/20)
This paper discloses the efficient palladium-catalyzed anti-Markovnikov oxidative acetalization of activated terminal olefins with iron(iii) sulfate as the reoxidant. This methodology requires mild reaction conditions and shows high regioselectivity toward anti-Markovnikov products and compatibility with a wide range of functional groups. Iron(iii) sulphate was the sole reoxidant used in this method. Various olefins like vinylarenes, aryl-allylethers, aryl or benzyl acrylates and homoallylic alcohols all reacted well providing anti-Markovnikov acetals, some of which represent orthogonally functionalized 1,3- and 1,4-dioxygenated compounds.
Palladium-Catalyzed Aerobic Synthesis of Terminal Acetals from Vinylarenes Assisted by π-Acceptor Ligands
Matsumura, Satoko,Sato, Ruriko,Nakaoka, Sonoe,Yokotani, Wakana,Murakami, Yuka,Kataoka, Yasutaka,Ura, Yasuyuki
, p. 751 - 757 (2017/03/13)
Terminal acetals were synthesized from various vinylarenes and 1,2- or 1,3-diols using a simple PdCl2(MeCN)2/methoxy-p-benzoquinone (MeOBQ)/CuCl catalyst system and 1 atm of O2 under mild reaction conditions by the anti-Markovnikov nucleophilic attack of an oxygen nucleophile on the coordinated vinylarenes. Cyclic α,β-unsaturated carbonyl compounds such as MeOBQ and N-phenylmaleimide were especially effective as additives to afford higher yields of the desired terminal acetals. Kinetic experiments indicated that MeOBQ operates as a π-acceptor ligand for Pd to accelerate the reaction and that the dissociation of a chloride ion from Pd precedes the rate-determining step.
