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

• Published in: Green chemistry : an international journal and green chemistry resource : GC 2023-01, Vol.25 (2), p.72-727
• Main Authors: Ma, Guolan, Xu, Chang, Yang, Shaoxiong, Zhu, Yanren, Ye, Silei, Qin, Rui, Zeng, Chongchong, Du, Wenqiang, Zhang, Hongbin, Chen, Jingbo
• Format: Article
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/d2gc04647d

The direct synthesis of β-NH 2 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 HCO 2 NH 4 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-NH 2 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-NH 2 alcohols that could be converted to diverse functionalized molecules with ease. The direct synthesis of β-NH 2 alcohols via flexible ammonolysis of epoxides is still a challenging and unresolved problem.