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Enabling Cyclopropanation Reactions of Imidazole Heterocycles via Chemoselective Photochemical Carbene Transfer Reactions of NHC-Boranes.

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Herein we report a site-selective cyclopropanation of N-heterocyclic carbene (NHC)-borane complexes via photochemical carbene transfer reactions. By subtle changes to the reaction conditions, this approach can be further extended toward… Click to show full abstract

Herein we report a site-selective cyclopropanation of N-heterocyclic carbene (NHC)-borane complexes via photochemical carbene transfer reactions. By subtle changes to the reaction conditions, this approach can be further extended toward the difunctionalization of NHC-boranes via cyclopropanation and the B-H insertion reaction. Further investigations in photochemical continuous-flow applications and synthetic transformations proved the utility of the method. Theoretical calculations and control experiments were performed to explain the observed selectivity.

Keywords: carbene transfer; transfer reactions; photochemical carbene; cyclopropanation; nhc boranes; carbene

Journal Title: Organic letters
Year Published: 2022

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