Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels
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 aq...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
American Chemical Society (ACS)
2022
|
| Online Access: | https://hdl.handle.net/1721.1/141239 |
| _version_ | 1826197059336667136 |
|---|---|
| author | Jun, Joomyung V Raines, Ronald T |
| author_facet | Jun, Joomyung V Raines, Ronald T |
| author_sort | Jun, Joomyung V |
| collection | MIT |
| description | 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. |
| first_indexed | 2024-09-23T10:41:47Z |
| format | Article |
| id | mit-1721.1/141239 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T10:41:47Z |
| publishDate | 2022 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1412392022-03-16T18:06:46Z Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels Jun, Joomyung V Raines, Ronald T 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. 2022-03-16T18:06:45Z 2022-03-16T18:06:45Z 2021 2022-03-16T18:02:58Z Article http://purl.org/eprint/type/JournalArticle https://hdl.handle.net/1721.1/141239 Jun, Joomyung V and Raines, Ronald T. 2021. "Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels." Organic Letters, 23 (8). en 10.1021/ACS.ORGLETT.1C00793 Organic Letters Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Jun, Joomyung V Raines, Ronald T Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels |
| title | Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels |
| title_full | Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels |
| title_fullStr | Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels |
| title_full_unstemmed | Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels |
| title_short | Two-Step Synthesis of α-Aryl-α-diazoamides as Modular Bioreversible Labels |
| title_sort | two step synthesis of α aryl α diazoamides as modular bioreversible labels |
| url | https://hdl.handle.net/1721.1/141239 |
| work_keys_str_mv | AT junjoomyungv twostepsynthesisofaaryladiazoamidesasmodularbioreversiblelabels AT rainesronaldt twostepsynthesisofaaryladiazoamidesasmodularbioreversiblelabels |