Palladium-Catalyzed Construction of Heteroatom-Containing π-Conjugated Systems by Intramolecular Oxidative C-H/C-H Coupling Reaction

Chemistry. 2015 Jun 1;21(23):8365-8. doi: 10.1002/chem.201501116. Epub 2015 Apr 23.

Abstract

Synthesis of heteroatom-containing ladder-type π-conjugated molecules was successfully achieved via a palladium-catalyzed intramolecular oxidative C-H/C-H cross-coupling reaction. This reaction provides a variety of π-conjugated molecules bearing heteroatoms, such as nitrogen, oxygen, phosphorus, and sulfur atoms, and a carbonyl group. The π-conjugated molecules were synthesized efficiently, even in gram scale, and larger π-conjugated molecules were also obtained by a double C-H/C-H cross-coupling reaction and successive oxidative cycloaromatization.

Keywords: CH activation; CH/CH coupling; heteroatom; palladium; pi-conjugated system.

Publication types

  • Research Support, Non-U.S. Gov't