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Synfacts 2008(6): 0625-0625  
DOI: 10.1055/s-2008-1072781
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

One-Pot Preparation of Hydroxyaryl- and (Hydroxyalkyl)aryltrifluoroborates

Rezensent(en):Paul Knochel, Tobias Thaler
Y. H. Park, H. R. Ahn, B. Canturk, S. I. Jeon, S. Lee, H. Kang*, G. A. Molander*, J. Ham*
University of Pennsylvania, Philadelphia, USA; Korea Institute of Technology, Kangnung National University, Kwandong University College of Medicine, Gangneung and Seoul National University, South Korea
A Facile One-Pot Preparation of Potassium Hydroxyaryl- and (Hydroxyalkyl)aryltrifluoroborates
Org. Lett.  2008,  10:  1215-1218  
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Publikationsverlauf

Publikationsdatum:
21. Mai 2008 (online)

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Key words

halogen-lithium exchange reaction - hydroxyaryltrifluoroborates - (hydroxyalkyl)aryltrifluoroborates - Suzuki-Miyaura cross-coupling - one-pot reaction

Significance

A simple one-pot synthesis of both potassium hydroxyaryl- and (hydroxyalkyl)aryltri­fluoroborates was developed. The respective hydroxyl groups are protected in situ via deproto­nation with t-BuLi. The hydroxylated trifluoroborates could be successfully subjected to Suzuki-Miyaura cross-coupling.

Comment

This method offers an easy one-pot access to various hydroxylated trifluoroborates. Organotrifluoroborates are often superior to their boronic acid or ester counterparts in Suzuki-Miyaura cross-coupling reactions where they are less subject to protodeboronation. Moreover, organotrifluoroborates are stable, crystalline solids that are easy to purify.

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