Bu₄NI Catalyzed C–N Bond Formation via Cross-Dehydrogenative Coupling of Aryl Ethers (C_sp3–H) and Tetrazoles (N–H)

Abstract

Intermolecular C-N bond formations via cross-dehydrogenative coupling (CDC) of aryl ethers and tetrazoles have been developed under a metal-free condition. In the presence of catalytic amount of tetrabutylammonium iodide (TBAI) and aqueous TBHP, aryl ethers coupled efficiently with tetrazoles to afford hemiaminal ethers. This strategy showed high level of regioselectivity for substrates possessing multiple sp(3) C-H bonds adjacent to the ethereal oxygen.