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An Improved Catalytic System, Pd(PPh3)4/PhCOOH Combined Catalyst, for the Allylation of Carbon Pronucleophiles with Allenes

Nitin T. Patil, Nirmal K. Pahadi, Yoshinori Yamamoto*

*Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Email:

N. T. Patil, N. K. Pahadi, Y. Yamamoto, Synthesis, 2004, 2186-2190.

DOI: 10.1055/s-2004-829178


The reaction of allenes with active methylenes proceeded smoothly in the presence of Pd(PPh3)4/PhCOOH to give the corresponding monoallylated products with E-stereoselectivity in good yields, whereas Pd2(dba)3·CHCl3/dppb as catalyst only affords allylation products in lower yield with lower stereoselectivities.

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proposed mechanism

Key Words

palladium, carboxylic acids, catalysis, allenes, C-nucleophiles

ID: J66-Y2004-2300