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.