N‑Arylation of DABCO with Diaryliodonium Salts: General Synthesis of N‑Aryl-DABCO Salts as Precursors for 1,4-Disubstituted Piperazines

Employing DABCO as a substrate, aryl­(mesityl)­iodonium triflates are introduced as arylating agents for a tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents of different electronic...

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Bibliographic Details
Published in:Organic letters 2018-10, Vol.20 (20), p.6389-6393
Main Authors: Bugaenko, Dmitry I, Yurovskaya, Marina A, Karchava, Alexander V
Format: Article
Language:English
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Summary:Employing DABCO as a substrate, aryl­(mesityl)­iodonium triflates are introduced as arylating agents for a tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents of different electronic natures. This metal-free methodology has no analogy among known transition-metal-based reactions. The utility of isolated N-aryl-DABCO salts is demonstrated for the preparation of flibanserin.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02676