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Synlett 2009(18): 2939-2942  
DOI: 10.1055/s-0029-1218000
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Tandem Catalytic Triple-Bond Cleavage of Alkyne in Association with Aldehyde, Alkene, and Water

Kyung-Mi Cha, Eun-Ae Jo, Chul-Ho Jun*
Department of Chemistry and Centre for Bioactive Molecular Hybrid (CBMH), Yonsei University, Seoul 120-749, Korea
Fax: +82(2)31472644; e-Mail: junch@yonsei.ac.kr;
Further Information

Publication History

Received 20 July 2009
Publication Date:
08 October 2009 (online)

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Abstract

In this tandem reaction the carbon-carbon triple bond of an alkyne is catalytically cleaved in association with aldehyde, al­kene, and H2O under catalyst mixtures of Rh(I), 2-amino-3-picoline, primary amine, and acid. The reaction starts with chelation-assisted hydroacylation of the alkyne with an aldehyde. The retro-Mannich-type fragmentation of the resulting α,β-unsaturated ketimine by an amine and acid affords a ketimine and an aldimine, which is trapped by an alkene and give ketones after hydrolysis.

Key words

C-C triple-bond cleavage - C-H bond activation - rho­dium - homogeneous catalysis

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