10.1021/ol5006246.s001
José-Antonio García-López
José-Antonio
García-López
Michael F. Greaney
Michael F.
Greaney
Use of 2‑Bromophenylboronic Esters as Benzyne
Precursors in the Pd-Catalyzed Synthesis of Triphenylenes
American Chemical Society
2015
aryne precursors
triphenylene compounds
benzyne mechanism
Benzyne Precursors
2015-12-17 01:57:12
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Use_of_2_Bromophenylboronic_Esters_as_Benzyne_Precursors_in_the_Pd_Catalyzed_Synthesis_of_Triphenylenes/2032569
<i>ortho</i>-Substituted
aryl boronates are introduced
as aryne precursors for transition-metal-catalyzed transformations.
On treatment with <sup><i>t</i></sup>BuOK and Pd(0), metal-bound
aryne intermediates are formed that undergo effective trimerization
to form useful triphenylene compounds. For <i>meta</i>-substituted
arynes, the 3:1 product ratio in favor of non-C<sub>3</sub> symmetric
material is indicative of a benzyne mechanism.