Nickel-Catalyzed C-O Cross-coupling of N-Boc-Protected Amino Alcohols with (Hetero)aryl Halides.

Authors

Zi-Han Zhao, Jia-Xin Feng, Gao-Dong Xu, Nan Ji, Liu Yang, Dong Xue, Wei He

Published in

The Journal of organic chemistry. Oct 21, 2026. Epub Oct 21, 2026.

Abstract

The aryloxyalkylamine motif is a privileged pharmacophore found in bioactive molecules. However, achieving its direct and chemoselective construction via O-arylation of amino alcohols remains a significant challenge in synthetic chemistry. Herein, we report a mild and efficient nickel-catalyzed C-O cross-coupling of N-Boc-protected amino alcohols with (hetero)aryl halides. This method employs bipyridine as the ligand and an organic amine as the base, circumventing the need for specific ligand systems and strong inorganic bases typically required in other protocols. The system exhibits excellent functional group tolerance and broad compatibility, particularly with regard to heteroaryl halides and amino alcohols derived from natural amino acids. Furthermore, the scalability of the reaction is demonstrated through gram-scale synthesis, highlighting its potential for practical applications.

PMID:
42901712
Bibliographic data and abstract were imported from PubMed on 21 Oct 2026.

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