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Updated: Jun 6, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Nickel-Catalyzed O-Arylation of N-Protected Amino Alcohols with (Hetero)aryl Chlorides
Kathleen M Morrison1, Emily C Jackson1, Erika M H Elliott1
1Department of Chemistry, Dalhousie University, 6274 Coburg Road, P.O. Box 15000, Halifax, Nova Scotia, B3H 4R2, Canada.
Abstract:
The aryloxyamine motif is a prominent pharmacophore in drug design and development. While these biologically relevant structures could in principle be sustainably assembled from the base metal-catalyzed O-arylation of inexpensive and abundant amino alcohols with (hetero)aryl chlorides, reports of such challenging C-O bond formations with useful scope are lacking. In response, we report herein the hitherto unknown Ni-catalyzed C-O cross-coupling of N-protected amino alcohols (primary, secondary, and tertiary) with (hetero)aryl chlorides. Also presented are chemoselective sequential/telescoped C-N and C-O cross-couplings of the unprotected amino alcohol prolinol to afford an unsymmetrical diarylated product.
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