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. 2014 Jun 1;1(4):426-429.
doi: 10.1039/C4QO00022F.

The Redox-A3 Reaction

Daniel Seidel

The Redox-A3 Reaction

Daniel Seidel. Org Chem Front. .

Abstract

This Highlight details the recent emergence of a new type of A3 reaction (three-component condensation of an amine, an aldehyde and an alkyne). In contrast to the classic A3 coupling process, the redox-A3 reaction incorporates an iminium isomerization step and leads to amine α-alkynylation. The overall transformation is redox-neutral by virtue of a combined reductive N-alkylation/oxidative C-H bond functionalization.

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Figures

Scheme 1
Scheme 1
The A3 vs. the redox-A3 reaction, mechanistic considerations.
Scheme 2
Scheme 2
A3 vs. redox-A3 reaction with pyrrolidine: Dependence of product ratios on the aldehyde.
Scheme 3
Scheme 3
Scope of the Cu(2-EH)2 catalyzed redox-A3 reaction by Seidel et al.
Scheme 4
Scheme 4
Evaluation of catalysts in the redox-A3 reaction with THIQ.
Scheme 5
Scheme 5
Scope of the CuI catalyzed redox-A3 reaction by Yu et al.
Scheme 6
Scheme 6
Scope of the enantioselective redox-A3 reaction by Ma et al.
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