Synfacts 2010(9): 0999-0999  
DOI: 10.1055/s-0030-1258010
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Synthesis of Isoquinolones

Contributor(s): Victor Snieckus, Timothy Hurst
N. Guimond, C. Gouliaras, K. Fagnou*
University of Ottawa, Canada
Further Information

Publication History

Publication Date:
23 August 2010 (online)

Significance

The rhodium(III)-catalyzed synthesis of isoquinolones 3 from hydroxamic acid derivatives 1 and acetylenes 2 is reported. The reaction is equally tolerant of EDGs and EWGs on the aromatic ring. For meta-substituted substrates the rhodation occurs exclusively at the least sterically hindered position leading to the C7-substituted isoquinolones. Symmetrical and unsymmetrical acetylenes both participate efficiently in the ­reaction. In the case of alkyl-aryl-disubstituted alkynes, the sp² center is installed selectively at the 3-position (R³). A mechanism is postulated on the basis of deuteration and competition experiments.