Palladium-catalyzed hydrocarbonation and hydroamination of 3,3-dihexylcyclopropene with pronucleophiles.
The reaction of 3,3-dihexylcyclopropene 1 with carbon and amine pronucleophiles 2 in the presence of palladium catalysts proceeded smoothly to give the corresponding hydrocarbonation products 3, allylated nucleophiles, in good to high yields. For example, in the presence of catalytic amounts of Pd(PPh(3))(4) and dppf, the reaction of 3,3-dihexylcyclopropene with ethyl 2-cyanopropionate and ethyl 2-cyanophenylacetate gave ethyl 2-cyano-2-methyl-4-undecenoate and ethyl 2-cyano-2-phenyl-4-undecenoate in 82 and 86% yield, respectively.
Nakamura
Itaru
I
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Bajracharya
Gan B
GB
Yamamoto
Yoshinori
Y
D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006146:Guanidines / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D006146:Guanidines; D006846:Hydrocarbons, Halogenated; D007202:Indicators and Reagents; D010165:Palladium