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Updated: Jul 6, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
One-pot tandem reduction and site-selective halogenation of nitroarenes
Ganesh Kumar Dhandabani1, Li-Te Chang1, Hao-Yu Hsieh2
1Center for Innovative Therapeutics Discovery, National Taiwan University, 17, Xuzhou Road, Room 936, Taipei 10055, Taiwan.
Abstract:
Halogenated aryl amines are a widely used chemical feedstock in the pharmaceutical and agrochemical industries. Achieving a single regioselective product from the para-selective halogenation of the aryl ring is significantly challenging because of the presence of several C-H bonds with similar reactivities. In this study, single para-halogenated aniline derivatives were prepared by the cascade para-selective halogenation (Cl, Br) and reduction of nitrobenzene derivatives using a mixture of SnCl2/SnCl4 salts. The mechanistic study confirmed that the noncovalent interactions between the chalcogen bond and Sn salt were pivotal for achieving regioselectivity. This synthetic method was applied for the development of potent and highly selective positron emission tomography molecular probes for serotonin transporters.
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