Remote-Group-Assisted Facile Oxidative Arylation of Furans and Pyrroles

A mild strategy for oxidative Csp2-H arylation of electron-rich furans and pyrroles has been achieved with the aid of remote carbonyl-containing groups. These groups enable the Pd-catalyzed oxidative Csp2-H arylation of furans to proceed under a warm temperature and O2 atmosphere, while distinctly promoting the yield of such a reaction for pyrroles. Supported by the experimental results and density functional theory calculation, an original concept, i.e., the remote-group-assisted Heck-type pathway, is proposed for these transformations. Moreover, the electron-rich substrates including the arylboronic acids as the arylating reagents were found to be well-tolerated, and the strategy has also been applied to the alternative route for synthesizing the skeleton of S-nitrosoglutathione reductase inhibitors.