121074-61-1Relevant articles and documents
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.
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
supporting information; experimental part, p. 1165 - 1167 (2012/02/04)
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.
