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. 2014 Feb 7;16(3):730-2.
doi: 10.1021/ol403431u. Epub 2013 Dec 13.

Redox-neutral α-arylation of amines

Weijie Chen  1 , Richard G Wilde, Daniel Seidel
Affiliations

Redox-neutral α-arylation of amines

Weijie Chen et al. Org Lett. .

Abstract

The direct α-arylation/N-alkylation of cyclic amines was achieved in a redox-neutral fashion under mild conditions. Transformations occur in the absence of any additives or are promoted by simple carboxylic acids.

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Figures

Scheme 1
Scheme 1
Concept for redox-neutral amine α-functionalization.
Scheme 2
Scheme 2
Initial results and optimized conditions for the α-arylation of pyrrolidine with β-naphthol.
Scheme 3
Scheme 3
Substrate scope for the α-arylationa a Reactions were performed on a 1 mmol scale. Yields correspond to the desired regioisomers. b Reactions with β-naphthols and indoles: Ar′H (1.5 equiv); reactions with phenols or pyrroles: Ar′H (5 equiv); reactions with indoles and pyrroles: 2-EHA (1 equiv). c 2.5 equiv of 2-EHA were used. d 2,5-Disubstituted pyrrole product was isolated as a byproduct in 19% yield (dr = 3:1).
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