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Synthesis 2012(8): 1233-1236
DOI: 10.1055/s-0031-1289747
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
Weitere Informationen
Received
22 December 2011
Publikationsdatum:
15. März 2012 (online)
Publikationsverlauf
Publikationsdatum:
15. März 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).