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Cascade C-H Activation and Defluorinative Annulation of 2-Arylbenzimidazoles with α-Trifluoromethyl-α-diazoketones: Modular Assembly of 6-Fluorobenzimidazo[2,1-]isoquinolines. | LitMetric

Cascade C-H Activation and Defluorinative Annulation of 2-Arylbenzimidazoles with α-Trifluoromethyl-α-diazoketones: Modular Assembly of 6-Fluorobenzimidazo[2,1-]isoquinolines.

Org Lett

State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China.

Published: July 2023

A novel Ru-catalyzed redox-neutral [4+2] cyclization of 2-arylbenzimidazoles with α-trifluoromethyl-α-diazoketones has been achieved through sequential C-H activation and defluorinative annulation. This synthetic protocol unlocks modular and expeditious access to 6-fluorobenzimidazo[2,1-]isoquinolines with high efficiency and excellent functional group compatibility. The resultant monofluorinated heterocyclic products can readily diversified by various nucleophiles.

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http://dx.doi.org/10.1021/acs.orglett.3c01296DOI Listing

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