B 2 (OH) 4 -Mediated Reductive Ring-Opening of N -Tosyl Aziridines by Nitroarenes: A Green and Regioselective Access to Vicinal Diamines

B 2 (OH) 4 -Mediated Reductive Ring-Opening of N -Tosyl Aziridines by Nitroarenes: A Green and Regioselective Access to Vicinal Diamines

The nucleophilic ring-opening of aziridine derivatives provides an important synthetic tool for the preparation of various β-functionalized amines. Amines as nucleophiles are employed to prepare synthetically useful 1,2-diamines in the presence of various catalysts or activators. Herein, the B (OH)...

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Veröffentlicht in:Journal of organic chemistry 2024-06, Vol.89 (12), p.8656-8667
Hauptverfasser: Pan, Mengni, Shen, Yue, Li, Yang, Shen, Chaoren, Li, Wanfang
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container_end_page 8667
container_issue 12
container_start_page 8656
container_title Journal of organic chemistry
container_volume 89
creator Pan, Mengni
Shen, Yue
Li, Yang
Shen, Chaoren
Li, Wanfang
description The nucleophilic ring-opening of aziridine derivatives provides an important synthetic tool for the preparation of various β-functionalized amines. Amines as nucleophiles are employed to prepare synthetically useful 1,2-diamines in the presence of various catalysts or activators. Herein, the B (OH) -mediated reductive ring-opening transformation of -tosyl aziridines by nitroarenes was developed. This aqueous protocol employed nitroarenes as cheap and readily available amino sources and proceeds under external catalyst-free conditions. Control experiments and DFT calculations pointed to the reduction of nitroarenes to aryl amines via -aryl boramidic acid ( ) and an S 1-type ring-opening of -tosylaziridines by the resultant aryl amines with high regioselectivity.
doi_str_mv 10.1021/acs.joc.4c00591
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title B 2 (OH) 4 -Mediated Reductive Ring-Opening of N -Tosyl Aziridines by Nitroarenes: A Green and Regioselective Access to Vicinal Diamines
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