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: yoshiyamamoto1.chem.tohoku.ac.jp

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

DOI: 10.1055/s-2004-829178

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Abstract

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.

see article for more examples

proposed mechanism

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Key Words

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

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ID: J66-Y2004-2300