Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols.

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

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.

ARYL chlorides; ARYLATION; MATERIALS handling; FUNCTIONAL groups; COMPLEX organizations; CHEMOSELECTIVITY; AMINO alcohols

Angewandte Chemie, 2023, Vol 135, Issue 23, p1

0044-8249

Academic Journal

10.1002/ange.202300686