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Synthesis 2018; 50(06): 1323-1330
DOI: 10.1055/s-0036-1591859
paper
© Georg Thieme Verlag Stuttgart · New York

Reductive N-Arylethylation of Aromatic Amines and N-Heterocycles with Enol Ethers

Katharina Vögerl
Department of Pharmacy – Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstr. 5–13, 81377 Munich, Germany   Email: Franz.Bracher@cup.uni-muenchen.de
,
Duc Nghia Ong
Department of Pharmacy – Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstr. 5–13, 81377 Munich, Germany   Email: Franz.Bracher@cup.uni-muenchen.de
,
Franz Bracher  *
Department of Pharmacy – Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstr. 5–13, 81377 Munich, Germany   Email: Franz.Bracher@cup.uni-muenchen.de
› Author Affiliations
Further Information

Publication History

Received: 07 October 2017

Accepted after revision: 11 November 2017

Publication Date:
12 December 2017 (online)

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Abstract

A convenient method for N-arylethylation of aromatic amines and heterocycles under mild reductive conditions was developed using (2-methoxyvinyl)(hetero)arenes as building blocks and triethylsilane/trifluoroacetic acid as reducing agent. This protocol is compatible with numerous functional groups, and aliphatic amines are inert due to protonation.

Key words

arylethylation - triethylsilane - aromatic amines - heterocycles - chemoselectivity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591859.
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