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Synfacts 2010(5): 0537-0537  
DOI: 10.1055/s-0029-1219683
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

1,2-Diborylation of Arynes

Contributor(s): Timothy M. Swager, William R. Collins
H. Yoshida*, K. Okada, S. Kawashima, K. Tanino, J. Ohshita
Hiroshima University, Japan
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

The authors report a platinum isocyanide complex catalyzed method for the diborylation of arynes. Utilizing this optimized catalyst, the authors can efficiently prepare a variety of 1,2-diborylarenes from readily available bis(pinacolato)diboron and silyl triflate aryne precursors. The synthetic utility of these products was demonstrated through several different Suzuki-Miyaura cross-coupling reactions. Both symmetrical, double cross-couplings, and tandem double, unsymmetrical cross-couplings occur in good yields. ­Additionally, it is possible to produce the mono cross-coupled product.