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Synfacts 2010(1): 0084-0084  
DOI: 10.1055/s-0029-1218429
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Ni-Catalyzed Neopentylglycolborylation of Aryl Chlorides

Contributor(s):Paul Knochel, Andrei Gavryushin
C. Moldoveanu, D. A. Wilson, C. J. Wilson, P. Corcoran, B. M. Rosen, V. Percec*
University of Pennsylvania, Philadelphia, USA
Neopentylglycolborylation of Aryl Chlorides Catalyzed by the Mixed Ligand System NiCl2(dppp)/dppf
Org. Lett.  2009,  11:  4974-4977  
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Publication History

Publication Date:
21 December 2009 (online)

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Key words

neopentylboranes - borylation - aryl chlorides - nickel

Significance

Neopentylglycolborane can be readily prepared from BH3˙SMe2 and the neopentylglycol. Its reaction with aryl chlorides in the presence of a nickel catalyst gives rise to aryl neopentyl boronates, which are stable derivatives of highly synthetically useful arylboronic acids. This is an interesting example of the application of a ‘mixed ligand’ catalytic system.

Comment

For a recent example of the palladium-catalyzed borylation of aryl chlorides, see: B. Bhayana, B. P. Fors, S. L. Buchwald Org. Lett. 2009, 11, 3954. As usual, aromatic bromides ­react faster than the chlorides. Bis-boronates can be easily prepared from bis-dichlorobenzenes. Functionalities such as acetyl, amide, or even a free phenolic hydroxyl are tolerated.

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