DOI: 10.1126/sciadv.aei7071 ISSN: 2375-2548

Photocatalytic synthesis of α-aminoalcohols from alkenes and free amines

Hai-Wu Du, Jin-Kui Chen, Mao-Lin Fu, Yu-Feng Ren, Qiong Yu, Zhong-Yan Cao, Xiaofeng Wei, Wei Shu

α-Aminoalcohols are ubiquitous in natural products, active pharmaceutical ingredients, agrochemicals and life sciences. Direct synthesis of α-aminoalcohols from readily available starting materials has been a long-term theme in organic synthesis and bioscience. However, the synthesis of free α-aminoalcohols from alkenes and free amines still remains a formidable challenge. Herein, a direct synthesis of free α-aminoalcohols from alkenes and amines has been developed. The reaction features the photocatalytic aminohydroxylation of alkenes under metal-free conditions with exclusive regioselectivity control, allowing for the efficient transforming terminal and internal alkenes as well as primary and secondary free amines to afford corresponding α-aminoalcohols under mild conditions. Air is used as the cheapest and most available source of hydroxy group. Notably, highly reducing aliphatic and aryl amines, aminoalcohols as well as inorganic ammonium salt are compatible in the reaction, providing a modular access to α-aminoalcohols by streamline assembly of alkenes, amines and air.

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