2234-20-0Relevant academic research and scientific papers
Iron-catalyzed, highly regioselective synthesis of α-aryl carboxylic acids from styrene derivatives and CO2
Greenhalgh, Mark D.,Thomas, Stephen P.
supporting information; experimental part, p. 11900 - 11903 (2012/09/07)
The iron-catalyzed hydrocarboxylation of aryl alkenes has been developed using a highly active bench-stable iron(II) precatalyst to give α-aryl carboxylic acids in excellent yields and with near-perfect regioselectivity. Using just 1 mol % FeCl2, bis(imino)pyridine 6 (1 mol %), CO 2 (atmospheric pressure), and a hydride source (EtMgBr, 1.2 equiv), a range of sterically and electronically differentiated aryl alkenes were transformed to the corresponding α-aryl carboxylic acids (up to 96% isolated yield). The catalyst was found to be equally active with a loading of 0.1 mol %. Preliminary mechanistic investigations show that an iron-catalyzed hydrometalation is followed by transmetalation and reaction with the electrophile (CO2).
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.
