A regioselective cross-dehydrogenative coupling between electron-deficient N-heterocycles (isoquinoline, quinolines, and quinoxalines) and methylbenzenes leading to regiospecific C-aroylation has been accomplished using AlCl3 as the catalyst in the presence of oxidant TBHP. This protocol is a practical alternative to the classical Minisci reaction.
An efficient metal free oxidative esterification of sp(3) C-H bonds (adjacent to an oxygen atom) in simple solvents like 1,4-dioxane, tetrahydropyran, tetrahydrofuran and ethyl acetate has been achieved using terminal aryl alkenes and alkynes as the ArCOO(-) sources.
tert-Butyl nitrite serves the dual role of an oxidant as well as a N1 synthon in a multicomponent reaction involving quinolines, isoquinolines, and styrenes. Herein, two sp C-H functionalizations of styrenes and one sp C-H functionalization of quinolines and isoquinolines lead to the formation of fused quinolines and isoquinolines via three sequential C-N bond formations.
A substrate-directed Pd-catalysed o-aroylation strategy has been demonstrated using new aroyl surrogates viz. terminal aryl alkenes and alkynes in the presence of TBHP. By a subtle change in catalyst from Cu to Pd, a differential selectivity is observed. While terminal aryl alkenes/alkynes in the presence of Cu/TBHP are reported to act as oaryloxy (ArCOO-) sources, the use of Pd/TBHP installs an aroyl (ArCO-) group at the ortho position with respect to the directing arenes.
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