Synfacts 2011(2): 0154-0154  
DOI: 10.1055/s-0030-1259251
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Cheap Precursor for Arynes

Contributor(s): Timothy M. Swager, Youhei Takeda
A. A. Cant, L. Roberts, M. F. Greaney*
University of Edinburgh and Pfizer Global R&D, Sandwich, UK
Further Information

Publication History

Publication Date:
19 January 2011 (online)

Significance

Trimerization of arynes is an efficient and versatile synthetic approach for triphenylenes. However, since the precursors for arynes require the presence of two adjacent leaving groups in a benzene ring, limitations regarding functionality and cost still remain. Herein, a straightforward method to generate arynes from benzoic acids, which are readily available and cheap, is reported. In the presence of a catalytic amount of a palladium catalyst, arynes are generated through C-H activation followed by decarboxylation, leading to triphenylenes selectively.