Transition metal-free ether coupling and hydroamidation enabling the efficient synthesis of congested heterocycles

Abstract

In this study, we discovered that α-bromocarboxamides react with alkynols containing tertiary alcohol moieties to produce congested ethers or heterocycles. Here, the etherification and hydroamidation reactions can be controlled by a suitable base. Both C–O and C–N bond formations occurred without a transition-metal catalyst. The stereospecific etherification and cyclization of diastereo-enriched α-bromocarboxamide afforded the corresponding diastereo-enriched ether and heterocyclic compound.