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. 2013 Mar 25;52(13):3765-9.
doi: 10.1002/anie.201300021. Epub 2013 Feb 25.

Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines

Deepankar Das  1 , Aaron X Sun, Daniel Seidel
Affiliations

Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines

Deepankar Das et al. Angew Chem Int Ed Engl. .

Abstract

A new strategy for iminium ion isomerization was applied to the direct, redox-neutral α-alkynylation of amines. Cu(II) 2-ethylhexanoate was identified as the optimal catalyst for this three-component coupling reaction of secondary amines, aldehydes and alkynes.

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Figures

Figure 1
Figure 1
Competing reaction pathways in the formation of isomeric propargylic amines.
Figure 2
Figure 2
Proposed Mechanism for α-Alkynylation.
Chart 1
Chart 1
Dependence of Product Ratios on the Aldehyde.
Chart 2
Chart 2
Scope of the Direct α-Alkynylation.
See this image and copyright information in PMC

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