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Synfacts 2014; 10(8): 0855
DOI: 10.1055/s-0034-1378494
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Trimerization of 2-Bromophenylboronic Esters via Metal-Bound Arynes

Contributor(s):
Paul Knochel
,
Thomas Klatt
García-López J.-A, Greaney MF * University of Manchester, UK
Use of 2-Bromophenylboronic Esters as Benzyne Precursors in the Pd-Catalyzed Synthesis of Triphenylenes.

Org. Lett. 2014;
16: 2338-2341
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Publication History

Publication Date:
18 July 2014 (online)

 
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Key words

arynes - aryl boronates - trimerization

Significance

The authors describe a synthetic protocol for the preparation of triphenylenes. 2-Bromophenylboronic esters were chosen as aryne precursors, which upon treatment with t-BuOK and Pd(0) undergo an effective trimerization. For meta-substituted arynes, the 3:1 product ratio in favor of non-C 3-symmetric material is an indicator for a benzyne mechanism.


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Comment

The used 2-bromophenylboronic esters are readily available over two steps starting from haloarene starting materials. The palladium catalyst initiates both benzyne formation and subsequent C–C bond-forming transformations.


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