One-pot tandem reduction and site-selective halogenation of nitroarenes

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 reac...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-01, Vol.22 (5), p.976-981
Main Authors: Dhandabani, Ganesh Kumar, Chang, Li-Te, Hsieh, Hao-Yu, Shih, Chia-Ling, Hsin, Ling-Wei
Format: Article
Language:English
Subjects:
Agrochemicals
Amines
Aniline
Aromatic compounds
Chalcogen bonds
Halogenation
Nitrobenzene
Positron emission
Positron emission tomography
Reduction
Regioselectivity
Serotonin
Serotonin transporter
Stannic chloride
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Summary: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 SnCl 2 /SnCl 4 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. Halogenated aryl amines are a widely used chemical feedstock in the pharmaceutical and agrochemical industries.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01732j