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  • Title: Copper-Catalyzed, N-Directed Distal C(sp3)-H Functionalization toward Azepanes.
    Author: Yang JW, Tan GQ, Liang KC, Xu KD, Su M, Liu F.
    Journal: Org Lett; 2022 Oct 28; 24(42):7796-7800. PubMed ID: 36264027.
    Abstract:
    We herein report a copper-catalyzed formal [5 + 2] aza-annulation of N-fluorosulfonamides and 1,3-dienes/1,3-enynes for synthesis of structurally diverse alkene/alkyne-containing azepanes. The reaction features selective functionalization of distal unactivated C(sp3)-H bonds and a broad substrate scope, thus allowing the late-stage modification of pharmaceuticals and natural products. A radical mechanism involving 1,5-hydrogen atom transfer of N-radicals, facile coupling of alkyl radicals with 1,3-dienes/1,3-enynes, and the construction of azepane motifs via C-N bond formation is proposed.
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