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Synfacts 2009(5): 0545-0545  
DOI: 10.1055/s-0028-1088193
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Addition of Terminal Alkynes to Olefins Catalyzed by Fe(OTf)3

Contributor(s): Paul Knochel, Tobias Thaler
K. Kohno, K. Nakagawa, T. Yahagi, J.-C. Choi, H. Yasuda, T. Sakakura*
National Institute of Advanced Industrial Science and Technology, Tsukuba and University of Tsukuba, Japan
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

A novel Lewis acid catalyzed addition of terminal alkynes to olefins was developed. Hereby, Fe(OTf)3 efficiently catalyzes this C-C bond-forming reaction at high temperatures. The addition reaction is in accordance with Markovni­kov’s rule, as observed in the addition of terminal acetylenes to styrenes, thus hinting to a cation-based catalytic cycle. The reaction also proceeds under air albeit with lower yields.