PIFA-Mediated Cross-Dehydrogenative Coupling of N-Heteroarenes with Cyclic Ethers: Ethanol as an Efficient Promoter

Ethanol is typically used in organic synthesis as an environmentally benign solvent. Herein, we report a mild and efficient cross-dehydrogenative coupling (CDC) reaction of N-heteroarenes with cyclic ethers by uncovering the new reactivity of ethanol as an efficient promoter in PIFA-mediated radical process. The reaction proceeds smoothly under the irradiation of visible light and features excellent functional group compatibility, which allows the expedite synthesis of a variety of medicinally valuable C alpha-heteroarylated cyclic ethers in moderate to high yields.

Automated summary

The study demonstrates the use of ethanol as an environmentally benign solvent in organic synthesis, showing its effectiveness as a promoter in PIFA-mediated radical process for the cross-dehydrogenative coupling reaction of N-heteroarenes with cyclic ethers. The reaction proceeds smoothly under visible light irradiation and allows for the rapid synthesis of various medicinally valuable C alpha-heteroarylated cyclic ethers with excellent functional group compatibility in moderate to high yields.