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Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels.

ABSTRACT: 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.

SUBMITTER: Jun JV

PROVIDER: S-EPMC8081586 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels.

Jun Joomyung V JV Raines Ronald T RT

Organic letters 20210405 8

α-Aryl-α-diazoamides were synthesized in two steps under mild conditions. This expeditious route employs Pd-catalyzed C-H arylation of <i>N</i>-succinimidyl 2-diazoacetate to obtain <i>N</i>-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. ...[more]

PMID: 33818092

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