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Synfacts 2010(3): 0294-0294
DOI: 10.1055/s-0029-1219259
DOI: 10.1055/s-0029-1219259
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
Iridium-Catalyzed Cascade Formation of Benzofulvenes
K. Tsuchikama, M. Kasagawa, K. Endo, T. Shibata*
Waseda University, Tokyo, Japan
Further Information
Publication History
Publication Date:
18 February 2010 (online)
Significance
The authors report an efficient and rapid method for the synthesis of indenes from readily available aryl ketones and diaryl alkynes. Based upon previous efforts from the Shibata laboratories (K. Tsuchikama et al. J. Organomet. Chem. 2008, 693, 3939) this reaction is suggested to proceed initially by an iridium alkynylation at the ortho C-H position on the arene. The resultant vinyl arene then undergoes a cationic, iridium-induced addition to the ketone. Subsequent dehydration produces the desired products in moderate to good yields.