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DOI: 10.1055/s-0034-1378510
Organocatalytic Oxidative Annulation of Benzamides with Alkynes
Publication History
Publication Date:
18 July 2014 (online)
Significance
The Antonchick group reports the first metal-free catalytic oxidative annulation of benzamide derivatives with alkynes. Using iodobenzene as catalyst and peracetic acid as the terminal oxidant, the desired isoquinolones were obtained in moderate to high yields (46–85%) under mild reaction conditions (ambient temperature) and short reaction times (30–240 min). High regioselectivity was observed when unsymmetrical diarylacetylenes were used.
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Comment
Until now the annulation of alkynes and benzamides to form isoquinolines and isoquinolones through C–H bond functionalization was only achieved by transition-metal catalysis. In their report the authors offer a mild and highly efficient organocatalytic alternative. Possible advantage of this method is its high regioselectivity using unsymmetrical diarylacetylenes, which was not observed in the transition-metal-catalyzed reactions.
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