Rhodium(III)-catalyzed isoquinolone synthesis: the N-O bond as a handle for C-N bond formation and catalyst turnover.
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.
Guimond
Nicolas
N
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada. nguim025@uottawa.ca
Gouliaras
Christina
C
Fagnou
Keith
K
D000480:Alkynes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006877:Hydroxamic Acids / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*
D000480:Alkynes; D006877:Hydroxamic Acids; D015363:Quinolones; D002244:Carbon; D012238:Rhodium; C006696:benzohydroxamic acid; D009584:Nitrogen; D010100:Oxygen