Categories: C-C Bond Formation > Nitrogen-containing molecules >

Synthesis of Hydroxylamines and Derivatives

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Recent Literature

An iridium photocatalyst enables the addition of fluorinated groups to nitrones using ascorbic acid as a stoichiometric reducing agent. Partially fluorinated alkyl iodides can also be effectively used. The resulting hydroxylamines can be readily converted to valuable fluorinated amines by reduction with zinc.
V. I. Supranovich, V. V. Levin, M. I. Struchkova, A. D. Dilman, Org. Lett., 2018, 20, 840-843.

An efficient Cu-catalyzed enantioselective alkyne addition to a wide range of nitrones utilizing tunable axially chiral imidazole-based P,N-ligands provides chiral propargyl N-hydroxylamines in good yields and enantioselectivity. A diverse array of optically active nitrogen-containing compounds can be accessed through facile transformations of the reaction products.
S. Yin, K. N. Weeks, A. Aponick, J. Am. Chem. Soc., 2024, 146, 7185-7190.