Treatment of alkyl α-(-heteroaryl)-α-diazoacetates with alkylating reagents affords diazoacetate N-heteroarenium salts. These novel 'onium' diazo compounds are mostly yellow solids, displaying increased thermal and acid stability. Their tetrafluoroborates undergo rhodium catalyzed [2 + 1] and Doyle-Kirmse reactions under mild conditions, suggesting the -quaternization an effective means of elimination of -coordination caused catalyst toxicity.
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http://dx.doi.org/10.1039/d4ob01056f | DOI Listing |
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