AlCl3‑Mediated CHF2 Transfer and Cyclocondensation of Difluoromethoxy Functionalized o‑Phenylenediamines to Access N‑Substituted Benzimidazoles

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 t...

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Bibliographic Details
Published in:Organic letters 2022-08, Vol.24 (33), p.6142-6147
Main Authors: Vinayagam, Vinothkumar, Karre, Satish Kumar, Kasu, Sreenivasa Reddy, Srinath, Ravuri, Naveen Babu Bathula, Hema Sundar, Sadhukhan, Subir Kumar
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02231