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Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels
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α-Aryl-α-diazoamides were synthesized in two steps under mild conditions. This expeditious route employs Pd-catalyzed C-H arylation of N-succinimidyl 2-diazoacetate to obtain N-succinimidyl 2-aryl-2-diazoacetates, followed by aminolysis. The ensuing diazo compounds can esterify carboxyl groups in aqueous solution, and the ester products are substrates for an esterase. The broad scope of the synthetic route enables the continued development of diazo compounds in chemical biology.
Date issued
2021Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Jun, Joomyung V and Raines, Ronald T. 2021. "Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels." Organic Letters, 23 (8).
Version: Author's final manuscript