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

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

References and Notes

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