Expedient Cyano-hydroxylation of Alkenes Enabled by Halogen Atom Transfer Induced Radical Ring-Opening Elaboration of 3-Bromo-isoxazoline Cycloadducts
Hui Wang , Qing Chen , Shuhui Wang , Cheng-Qiang Wang , Chao Feng
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (16) : 2015 -2020.
Expedient Cyano-hydroxylation of Alkenes Enabled by Halogen Atom Transfer Induced Radical Ring-Opening Elaboration of 3-Bromo-isoxazoline Cycloadducts
Herein, we present a highly efficient one-pot, two-step synthesis of β-hydroxy nitrile scaffolds, which possess both significant synthetic value and notable biological activity, starting from readily accessible alkenes. This methodology relies crucially on the seamless integration of a highly regioselective (3+2) cycloaddition reaction, employing the commercially available 1,1-dibromoformaldoxime as the 1,3-dipole precursor, with a subsequent halogen atom transfer-induced radical ring-opening elaboration of the resulting 3-bromo-2-isoxazoline cycloadducts. This protocol is featured by mild reaction conditions, broad alkene scope and various derivatizations of the obtained cyano-hydroxylation products, offering a versatile and practical pathway to accessing multi-functionalized molecules.
Cyano-hydroxylation / Alkenes / Halogen atom transfer / β-Hydroxy nitriles / Photoredox catalysis / Synthetic methods / Regioselectivity
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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