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

作者：Jiang, Kai; Wang, Haohao; Xie, Yi; Jiang, Huanfeng; Lei, Ming^*; Yin, Biaolin^*

来源：ACS Catalysis, 2023, 13(6): 3520-3531.

DOI：10.1021/acscatal.2c05936

• electron-rich heteroarenes
• oxidative arylation
• RGA Heck insertion
• remote groups
• mild condition

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 path-way, 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.

• 单位
  北京化工大学