ol5006246_si_001.pdf (6.22 MB)
Use of 2‑Bromophenylboronic Esters as Benzyne Precursors in the Pd-Catalyzed Synthesis of Triphenylenes
journal contribution
posted on 2015-12-17, 01:57 authored by José-Antonio García-López, Michael F. Greaneyortho-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.