Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels
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nihms-1691649.pdf
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Accepted version
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779.61 KB
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98597382a843b85e51745dd3f7868fe4
Author(s)
Jun, Joomyung V.
Raines, Ronald T.
Date Issued
April 2021
Journal
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
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
Koch Institute for Integrative Cancer Research at MIT
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/acs.orglett.1c00793
