Use of 2-bromophenylboronic esters as benzyne precursors in the Pd-catalyzed synthesis of triphenylenes

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ortho-Substituted aryl boronates are introduced as aryne precursors for transition-metal-catalyzed transformations. On treatment with tBuOK and Pd(0), metal-bound aryne intermediates are formed that undergo effective trimerization to form useful triphenylene compounds. For meta-substituted arynes, the 3:1 product ratio in favor of non-C3 symmetric material is indicative of a benzyne mechanism. © 2014 American Chemical Society.

Bibliographical metadata

Original languageEnglish
Pages (from-to)2338-2341
Number of pages3
JournalOrganic Letters
Issue number9
StatePublished - 2 May 2014