American Chemical Society
jo9b02502_si_002.cif (544.06 kB)

Photoredox-Mediated Remote C(sp3)–H Heteroarylation of N‑Alkyl Sulfonamides

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posted on 2019-12-10, 20:42 authored by Zhiqiang Deng, Guo-Xing Li, Gang He, Gong Chen
A Minisci-type δ-selective C­(sp3)–H heteroarylation of sulfonyl-protected primary aliphatic amines with N-heteroarenes under photoredox-catalyzed conditions was developed. The reaction typically uses a slight excess of amine reactant. The use of benziodoxole acetate (BI-OAc) oxidant and hexafluoroisopropanol solvent is critical to achieve high yield. Besides methylene C–H bonds, heteroarylation reactions of δ methyl C–H bonds also worked under more forced conditions. The reactions show a broad scope for both amine and N-heteroarene substrates, offering a straightforward method for synthesis of complex δ-heteroarylalkylmines from simple precursors.