Visible Light Mediated N-Desulfonylation of N-Heterocycles using a Heteroleptic Copper (I) Complex as a Photocatalyst

    • Cameron J. Hunter
    • Michael J. Boyd
    • Gregory D. May
    • Robert Fimognari*
    • Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, Massachusetts 02210, United States

    A photoredox protocol that uses a heteroleptic Cu (I) complex [Cu(dq)(BINAP)]BF4 has been developed for the photodeprotection of benzenesulfonyl protected N-heterocycles. A range of substrates were examined, including indazoles, indoles, pyrazoles, and benzimidazole, featuring both electron-rich and electron-deficient substituents, giving good yields of the N-heterocycle products with broad functional group tolerance. This transformation was also found to be amenable to flow reaction conditions.

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