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. 2023 Jun 5;62(23):e202300686.
doi: 10.1002/anie.202300686. Epub 2023 Apr 26.

Nickel-Catalyzed Chemoselective Arylation of Amino Alcohols

Kathleen M Morrison  1 , Charles S Yeung  2 , Mark Stradiotto  1
Affiliations

Nickel-Catalyzed Chemoselective Arylation of Amino Alcohols

Kathleen M Morrison et al. Angew Chem Int Ed Engl. .

Abstract

A systematic evaluation of competitive bisphosphine/Ni-catalyzed C-N versus C-O cross-couplings involving model compounds enabled development of hitherto unknown chemoselective O- and N-arylation of amino alcohols with (hetero)aryl chloride electrophiles, without recourse to protection group chemistry. Use of the CyPAd-DalPhos pre-catalyst C2 enabled particularly challenging O-arylation chemoselectivity in amino alcohols featuring branched primary and secondary alkylamine groups, while selective N-arylation was observed in substrates featuring less-hindered linear alkylamine and aniline reacting groups. Useful reaction scope in the (hetero)aryl chloride was achieved throughout, and the ability to conduct such transformations using benchtop handling of materials is demonstrated.

Keywords: Amino Alcohol; Bisphosphine; Chemoselectivity; Cross-Coupling; Nickel.

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