1244556-55-5Relevant articles and documents
Enantioselective Allylic Alkylation with 4-Alkyl-1,4-dihydro-pyridines Enabled by Photoredox/Palladium Cocatalysis
Zhang, Hong-Hao,Zhao, Jia-Jia,Yu, Shouyun
, p. 16914 - 16919 (2018)
Highly regio- and enantioselective allylic alkylation has been achieved enabled by the merger of photoredox and palladium catalysis. In this dual catalytic process, alkyl radicals generated from 4-alkyl-1,4-dihydropyridines act as the coupling partners of the π-allyl palladium complexes. The generality of this method has been illustrated through the reaction of a variety of allyl esters with 4-alkyl-1,4-dihydropyridines. This mechanistically novel strategy expands the scope of the traditional Pd-catalyzed asymmetric allylic alkylation reaction and serves as its alternative and potential complement.
Rhodium-catalyzed allylation of benzyl acetates with allylsilanes
Onodera, Gen,Yamamoto, Eriko,Tonegawa, Shota,Iezumi, Makoto,Takeuchi, Ryo
scheme or table, p. 2013 - 2021 (2011/10/09)
Benzyl acetate reacted with allyltrimethylsilane to give an allylation product in the presence of a catalytic amount of the (cyclooctadiene)rhodium(I) chloride dimer {[Rh(cod)Cl]2}, sodium tetrakis[3,5- bis(trifluoromethyl)phenyl]borate (NaBARF), and triphenyl phosphite [P(OPh) 3] in refluxing 1,2-dichloroethane. Primary, secondary and tertiary benzyl acetates could be used for the reaction. Moreover, allylation of gem-benzyl acetate was possible with [Rh(cod)Cl]2, NaBARF, and P(OPh)3. Monoallylation and diallylation of gem-benzyl acetate could be controlled by altering the reaction conditions. Cationic rhodium species generated in situ act as a Lewis acid catalyst to give a benzyl carbocation by elimination of the acetoxy group from the benzylic carbon. Copyright