5706-24-1Relevant academic research and scientific papers
Nickel-Catalyzed Domino Heck-Type Reactions Using Methyl Esters as Cross-Coupling Electrophiles
Zheng, Yan-Long,Newman, Stephen G.
, p. 18159 - 18164 (2019/11/13)
While esters are frequently used as traditional electrophiles in substitution chemistry, their application in cross-coupling chemistry is still in its infancy. This work demonstrates that methyl esters can be used as coupling electrophiles in Ni-catalyzed Heck-type reactions through the challenging cleavage of the C(acyl)?O bond under relatively mild reaction conditions at either 80 or 100 °C. With the σ-NiII intermediate generated from the insertion of acyl NiII species into the tethered C=C bond, carbonyl-retentive products were formed by domino Heck/Suzuki–Miyaura coupling and Heck/reduction pathways when organoboron and mild hydride nucleophiles are used.
Dependence of Aryl Ether Acylation upon Lewis Acid Stoichiometry
Buckley, Thomas F.,Rapoport, Henry
, p. 3056 - 3062 (2007/10/02)
Acylation of alkyl aryl ethers has been observed to be uniquely dependent on the stoichiometry of the Friedel-Crafts catalyst.With 100 molpercent catalyst, acylation proceeds rapidly and in high yield; with large molar excesses of catalyst, the reaction is essentially completely arrested.This inhibition can be reversed by using sterically bulky alkyl groups which effectively prevent complexing between catalyst and aryl ether.Based on these observations, we have developed processes for regioselective intramolecular acylation of either a phenyl or an alkoxylated phenyl ring when both are present.
