27795-83-1Relevant academic research and scientific papers
A Study of Polarization and Directing Effects of Unsymmetrical Alkynes Using Regioselective Pd-Catalyzed Bromoallylation
Topolov?an, Nikola,Hara, Shuto,Císa?ová, Ivana,To?ner, Zdeněk,Kotora, Martin
, p. 234 - 240 (2020)
Herein is disclosed the first comprehensive study of factors that affect the regioselectivity of PdBr2(PhCN)2-catalyzed bromoallylation of unsymmetrically substituted internal alkynes. The study was performed on a wide array of electronically and structurally diverse alkynes with aryl-aryl, aryl-ferrocenyl, and aryl-alkyl substitutions. The regioselective formation of bromoallylation products was mostly driven by the polarization of the triple bond in aryl-aryl and aryl-ferrocenyl-substituted ethynes. On the other hand, directing effect, which arises from the presence of a directing group in the side-chain of aryl-alkyl-substituted alkynes, was the dominating factor that determined the regioselectivity of these reactions.
