AlCl₃-Mediated CHF₂ Transfer and Cyclocondensation of Difluoromethoxy Functionalized o-Phenylenediamines to Access N-Substituted Benzimidazoles
2022
Vinayagam, Vinothkumar | Karre, Satish Kumar | Kasu, Sreenivasa Reddy | Srinath, Ravuri | Naveen Babu Bathula, Hema Sundar | Sadhukhan, Subir Kumar
Herein, we report for the first time a transition-metal-free frustrated Lewis pair (FLP) catalyzed CHF₂ group migration from an oxygen atom to the neighboring nitrogen atom, which led to the synthesis of N-substituted benzimidazoles at room temperature with excellent yields, broad functional group tolerance, and a short reaction time. The oxygen-attached difluoromethane acted as a C1 source in the synthesis of N-substituted benzimidazoles in the presence of AlCl₃ by cleaving one C–O bond and two C–F bonds, resulting in formation of two new C–N bonds.
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