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Synthesis 2012(8): 1233-1236  
DOI: 10.1055/s-0031-1289747
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Aryl Triolborates via Nickel-Catalyzed Borylation of Aryl Halides with 5-(tert-Butyldimethylsiloxymethyl)-5-methyl-1,3,2-dioxaborinane

Yosuke Sogabe, Takeshi Namikoshi, Shinji Watanabe, Miki Murata*
Department of Materials Science and Engineering, Kitami Institute of Technology, 165 Koencho, Kitami 090-8507, Japan
Fax: +81(157)264973; e-Mail: muratamk@mail.kitami-it.ac.jp;
Further Information

Publication History

Received 22 December 2011
Publication Date:
15 March 2012 (online)

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Abstract

The nickel-catalyzed borylation of aryl halides with 5-(tert-butyldimethylsiloxymethyl)-5-methyl-1,3,2-dioxaborinane, prepared in situ, was achieved. The mild reaction conditions allowed common functional groups in the aryl halides to be tolerated. The products of this borylation are potential precursors of aryl triolborates.

Key words

carbon-boron bond formation - nickel catalysis - cross-coupling - aryl halides - hydroboranes

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Our attempts to isolate 5-(hydroxymethyl)-5-methyl-1,3,2-dioxaborinane also failed. Furthermore, the use of 1,1,1-tris(hydroxymethyl)ethane instead of 1 for the one-pot nickel-catalyzed borylation was lacking in reactivity and reproducibility (0-50% yield).