63519-71-1Relevant academic research and scientific papers
Practical Intermolecular Hydroarylation of Diverse Alkenes via Reductive Heck Coupling
Gurak, John A.,Engle, Keary M.
, p. 8987 - 8992 (2018/09/11)
The hydroarylation of alkenes is an attractive approach to construct carbon-carbon (C-C) bonds from abundant and structurally diverse starting materials. Herein we report a palladium-catalyzed reductive Heck hydroarylation of aliphatic and heteroatom-substituted terminal alkenes and select internal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective with terminal alkenes and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of this method to complex molecule diversifications are demonstrated. Mechanistic experiments are consistent with a mechanism in which the key alkylpalladium(II) intermediate is intercepted with formate and undergoes a decarboxylation/C-H reductive elimination cascade to afford the saturated product and turn over the cycle.
THE EFFECT OF para-SUBSTITUENTS ON THE CONFORMATIONAL BEHAVIOUR OF AROMATIC SIDECHAINS
Cook, Michael J.,Khan, Tauqeer A.,Nasri, Khalida
, p. 249 - 258 (2007/10/02)
Proton nmr data are reported for some 2-aryl-1-propyl methyl esters, 2-aryl-1-propyl acetates and trifluoroacetates, 2-aryl-1-propanols and 4-aryl-2,2-dimethylpentanes.The vicinal coupling constants show that there is an increasing population of gauche Aryl/OR rotamers in the first three series (R = Me, R = COMe and R = COCF3) as electron donor groups on the aromatic ring are replaced by electron withdrawing groups.The results are ascribed to a gauche Aryl --- O interaction, the possible origins of which are discussed.
