Synfacts 2007(1): 0114-0114  
DOI: 10.1055/s-2006-955697
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

α-Alkylation of Nitriles Promoted by Hydrotalcite-Supported Catalysts

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada
K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, K. Kaneda*
Osaka University, Japan
Further Information

Publication History

Publication Date:
15 December 2006 (online)

Significance

A ruthenium-grafted hydrotalcite (Ru/HT) and hydrotalcite-supported palladium nanoparticles (Pdnano/HT) were readily prepared by treatment of hydrotalcite [HT; Mg6Al2(OH)16CO3] with aqueous RuCl3·nH2O and K2PdCl4, respectively. Ru/HT promoted the α-alkylation of benzylic cyanides with primary alcohols under Ar atmosphere to give the corresponding α-alkylated nitriles in 37-99% yield while the α-alky­lation of malononitrile and ethyl cyanoacetate did not occur. Pdnano/HT promoted the α-alkylation of benzylic cyanides and ethyl cyanoacetate with benzylic aldehydes followed by hydrogenation to afford α-alkylated nitriles in 19-99% yield, whereas the reaction of acetophenone with malononitrile did not proceed.