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Rhodium(III)-catalyzed isoquinolone synthesis: the N-O bond as a handle for C-N bond formation and catalyst turnover.

Journal of the American Chemical Society (2010-05-04)
Nicolas Guimond, Christina Gouliaras, Keith Fagnou
RÉSUMÉ

An external-oxidant-free process to access the isoquinolone motif via cross-coupling/cyclization of benzhydroxamic acid with alkynes is described. The reaction features a regioselective cleavage of a C-H bond on the benzhydroxamic acid coupling partner as well as a regioselective alkyne insertion. Mechanistic studies point out the important involvement of a N-O bond as a tool for C-N bond formation and catalyst turnover.

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Sigma-Aldrich
Benzhydroxamic acid, 99%