Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

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.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols ; day:26 ; month:04 ; year:2023 ; extent:7
Angewandte Chemie / International edition. International edition ; (26.04.2023) (gesamt 7)

Creator
Morrison, Kathleen M.
Yeung, Charles S.
Stradiotto, Mark

DOI
10.1002/anie.202300686
URN
urn:nbn:de:101:1-2023042715171010842429
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
14.08.2025, 11:00 AM CEST

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