68083-55-6Relevant academic research and scientific papers
Hypoiodite-catalyzed regioselective oxidation of alkenes: An expeditious access to aldehydes in aqueous micellar media
Swamy, Peraka,Reddy, Marri Mahender,Naresh, Mameda,Kumar, Macharla Arun,Srujana, Kodumuri,Durgaiah, Chevella,Narender, Nama
, p. 1125 - 1130 (2015/04/22)
A highly anti-Markovnikov selective oxidation of alkenes based on in situ generated hypoiodite catalysis in aqueous micellar media under mild conditions has been described. This novel catalytic system realizes an efficient synthesis of aldehydes from alkenes in an economically viable and environmentally safe fashion. The preliminary mechanistic studies suggest that the reaction proceeds via tandem iodofunctionalization/1,2-aryl or alkyl migration. The scope and limitations of this tandem process are demonstrated with various mono- and disubstituted (terminal and internal) olefins.
Novel anti-Markovnikov regioselectivity in the Wacker reaction of styrenes
Wright, Joseph A.,Gaunt, Matthew J.,Spencer, Jonathan B.
, p. 949 - 955 (2007/10/03)
The Wacker reaction is one of the longest known palladium-catalysed organic transformations, and in the vast majority of cases proceeds with Markovnikov regioselectivity. Palladium(II)-mediated oxidation of styrenes was examined and in the absence of reoxidants was found to proceed in an anti-Markovnikov sense, giving aldehydes. Studies on the mechanism of this unusual transformation were carried out, and indicate the possible involvement of a η4-palladium-styrene complex. With a heteropolyacid as the terminal oxidant, oxidation of styrene to give the anti-Markovnikov aldehyde as the major product was found to be catalytic.
Aromatic β-silylethenylation reactions via organogallium compounds
Kido, Yoshiyuki,Yoshimura, Satoru,Yamaguchi, Masahiko,Uchimaru, Tadafumi
, p. 1445 - 1458 (2007/10/03)
In the presence of GaCl3, silylethyne reacted electrophilically with aromatic hydrocarbons to give β-silylethenylated arenes. The reaction proceeded via cationic species generated by the interaction of GaCl3 and silylethyne. High reactivity of the intermediate was demonstrated by the rapid reaction rate at -78 °C using close to the equimolar amount of the substrates. ipso-Substitution reaction took place with 1,2,3- trimethoxybenzene. Structures and properties of several organogallium compounds involved in the reactions are discussed.
