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Updated: Jul 12, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Unified Synthesis of Unconventional α-Polyhalogenated Amines Through Hydroaminoalkylation
Angela K Hofmeister1, Giulia Iannelli1, Péter Angyal1
1Institute of Organic Chemistry, University of Vienna, Vienna, Austria.
Abstract:
We report a unified method for the synthesis of α-polyhalomethyl amines from alkenes and alkynes, enabled by readily available hemiaminal reagents. This operationally simple transformation allows for the introduction of not only well-established CF3 and CF2H groups, but also the synthetically (and medicinally) underexplored CF2Cl and CFClH motifs-thereby broadening access to previously inaccessible chemical space of halogenated amine scaffolds. The method displays broad substrate scope and functional-group tolerance while operating under mild conditions. Late-stage functionalization of drug-like derivatives of Oxaprozin, Erlotinib, and Ibuprofen (among others) is reported.
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