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Synfacts 2010(8): 0959-0959  
DOI: 10.1055/s-0030-1257795
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Borylation of Arenes Catalyzed by γ-Fe2O3

Contributor(s):Yasuhiro Uozumi, Takao Osako
G. Yan, Y. Jiang, C. Kuang*, S. Wang, H. Liu, Y. Zhang, J. Wang*
Tongji University, Shanghai and Peking University, Beijing, P. R. of China
Nano-Fe2O3 Catalyzed Direct Borylation of Arenes
Chem. Commun.  2010,  46:  3170-3172  
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Publication History

Publication Date:
22 July 2010 (online)

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Key words

maghemite - direct borylation - arenes - bis(pinacolato)diborane

Significance

γ-Fe2O3 magnetic nanoparticles (particle size 58 nm) catalyzed the borylation of arenes with bis(pinacolato)diborane in the presence of di-tert-butyl peroxide and potassium carbonate under air to give the corresponding borylated products in up to 75% yield (10 examples, eq. 1). A sequential reaction via γ-Fe2O3-catalyzed borylation of benzene and Suzuki-Miyaura coupling with iodoarenes gave the corresponding biaryls in up to 56% yield (4 examples, eq. 2).

Comment

The catalytic activity of γ-Fe2O3 was superior to that of the other iron catalysts, such as FeCl3, FeBr3, FeF3, Fe(acac)3, Fe2(SO4)3, and Fe2O3. In the borylation of toluene and anisole, the ortho-borylated products were obtained as major regioisomers.

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