355015-07-5Relevant articles and documents
Control of regioselectivity in Pd(0)-catalyzed coupling-cyclization reaction of 2-(2′,3′-allenyl)malonates with organic halides
Ma, Shengming,Jiao, Ning,Zhao, Shimin,Hou, Hairong
, p. 2837 - 2847 (2002)
The regioselectivity in the Pd(0)-catalyzed coupling-cyclization of 2-(2′,3′-allenyl)malonates with organic halides is determined by the steric and electronic effects of both substrates. By deliberate control of the reaction conditions, the regioselectivity of this reaction can be tuned. With conditions A and B, the reaction afforded vinylic cyclopropane derivatives, while with conditions C and D, the reaction afforded cyclopentene derivatives in a highly selective manner. Under similar conditions, 1-alkenyl halides tend to form more three-membered cyclic products. The increased steric hindrance at the 2′-positon of the allene moiety and aryl halides favors the formation of five-membered cyclic products. The regioselectivity of the reaction may be explained by the comparison of the relative stabilities of syn- and anti-type π-allyl palladium intermediates.
Regio- and Stereoselective Nickel-Catalyzed Coupling of Boronic Acids with Allenoates
Liu, Yang,Daka, Mario,Bandini, Marco
, p. 3187 - 3196 (2018/08/17)
The Ni(II)-catalyzed cross-coupling of arylboronic acids with allenoates is documented. The high regio- and stereoselectivity of the process enables a wide range of β-aryl β,γ-unsaturated esters to be prepared in good to excellent yields (up to 95%) and high E / Z -selectivity. Additionally, [3+2]-cascade sequence was observed when 2-formylphenylboronic acid was employed.
