The trading of space for time under weakly activated catalysis: expeditious synthesis of β-NH2 alcohols via a direct ammonolysis of epoxides with ammonia

The direct synthesis of β-NH2 alcohols via flexible ammonolysis of epoxides is still a challenging and unresolved problem. Herein, we present a strategy of “trading space for time under weakly activated catalysis” and “shielding the reactivity of the product”, and thereby developed a novel single-st...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2023-01, Vol.25 (2), p.720-727
Main Authors: Ma, Guolan, Chang, Xu, Yang, Shaoxiong, Zhu, Yanren, Ye, Silei, Qin, Rui, Zeng, Chongchong, Du, Wenqiang, Zhang, Hongbin, Chen, Jingbo
Format: Article
Language:English
Subjects:
Alcohols
Alkylation
Ammonia
Ammonolysis
Biological activity
Catalysis
Chemical synthesis
Epoxides
Green chemistry
Substrates
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Summary:The direct synthesis of β-NH2 alcohols via flexible ammonolysis of epoxides is still a challenging and unresolved problem. Herein, we present a strategy of “trading space for time under weakly activated catalysis” and “shielding the reactivity of the product”, and thereby developed a novel single-step ammonolysis reaction of epoxides with ammonia. A stoichiometric amount of HCO2NH4 as an additive plays a dual role in the global activation of substrates and in completely suppressing the side reaction of excessive alkylation. A broad scope of substrates including terpene- and steroid-derived epoxides cleanly afforded the target β-NH2 alcohols in good to excellent yields under easily adjustable mild conditions. Furthermore, this synthetic protocol is metal-free and eco-friendly and could be used for the gram-scale synthesis of biologically active β-NH2 alcohols that could be converted to diverse functionalized molecules with ease.
ISSN:1463-9262
1463-9270
DOI:10.1039/d2gc04647d