Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins
作者:Ryosuke Matsubara、Alicia C. Gutierrez、Timothy F. Jamison
DOI:10.1021/ja209235d
日期:2011.11.30
Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzylchloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including
Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization–Wacker oxidation of terminal alkenes
Terphenylylalkanethiols with different chain length were synthesized using palladium-catalyzed cross-coupling reactions. While the thiols with two and three methylene groups were obtained via photoaddition of thiopivalic acid to the respective alkenes, the longer terphenylylalkanethiols were synthesized by two consecutive Kumada cross-coupling reactions followed by a Mitsunobu reaction for the introduction of the sulfur functionality.
Hydroboration polymerization between various dienes and monobromoborane–dimethyl sulfide complex produces poly(organoboron halide)s consisting of C–B bonds in the main chain and having B–Br bonds, which show characteristic properties as a polymeric Lewis acid.
Direct one-pot syntheses of 4-(ω -alkenyl)-benzonitriles in high yields have been achieved via the reaction of terephthalonitriledianion with allyl or co-alkenyl bromides in liquidammonia.