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Synfacts 2009(7): 0813-0813  
DOI: 10.1055/s-0029-1217232
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

ortho-Borylation of Arenes with a Silica-SMAP-Ir Catalyst

Contributor(s): Yasuhiro Uozumi, Takao Osako
S. Kawamorita, H. Ohmiya, K. Hara, A. Fukuoka, M. Sawamura*
Hokkaido University, Sapporo, Japan
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

A silica-supported monophosphine-Ir catalyst (Silica-SMAP-Ir) was prepared by treatment of Silica-SMAP with [Ir(OMe)(cod)]2. Silica-SMAP-Ir catalyzed the ortho-borylation of various functionalized arenes with bis(pinacol­ato)diboron to give the corresponding ortho-­borylated products in 50-108% yield (19 examples). 0.005 mol% of the catalyst also promoted the reaction of neat methyl benzoate (20 mmol) with bis(pinacolato)diboron (10 mmol) at 100 ˚C to afford ortho-borylated benzoate in 88% yield with high TON (20000).