Virtually irreversible intramolecular C-H activations are deleterious for aza-carbenes. A picolyl-tethered cyclic(alkyl)(amino)carbene (CAAC) isomerizes into a donor-acceptor cyclopropane in this manner but restores the CAAC status by retro-C-H activation in… Click to show full abstract
Virtually irreversible intramolecular C-H activations are deleterious for aza-carbenes. A picolyl-tethered cyclic(alkyl)(amino)carbene (CAAC) isomerizes into a donor-acceptor cyclopropane in this manner but restores the CAAC status by retro-C-H activation in the presence of trapping agents like Se or CuCl. The same DA cyclopropane is readily hydrolyzed to a pyrrolidin-2-ol that acts as another picoCAAC precursor by undergoing 1,1-dehydration in the presence of Se or CuCl. The chemistry is distinct from the N-heterocyclic carbene analogue throughout.
Journal Title: Organic letters
Year Published: 2023
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