Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis
A rapid carboxylic acid-promoted lactone aminolysis is reported. A number of carboxylic acids were found to promote this amide bond-forming transformation, with aliphatic acids being the most efficient. This reaction is an equilibrium process (K[subscript eq] ≈ 1.8), and mechanistic investigations a...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2013
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| Online Access: | http://hdl.handle.net/1721.1/76282 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1826191939685318656 |
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| author | Foley, Megan A. Jamison, Timothy F. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Foley, Megan A. Jamison, Timothy F. |
| author_sort | Foley, Megan A. |
| collection | MIT |
| description | A rapid carboxylic acid-promoted lactone aminolysis is reported. A number of carboxylic acids were found to promote this amide bond-forming transformation, with aliphatic acids being the most efficient. This reaction is an equilibrium process (K[subscript eq] ≈ 1.8), and mechanistic investigations are consistent with mediation of a kinetically important proton-transfer step by the carboxylate, i.e., the conjugate base of the acid employed. |
| first_indexed | 2024-09-23T09:03:42Z |
| format | Article |
| id | mit-1721.1/76282 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T09:03:42Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/762822022-09-26T10:09:36Z Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis Foley, Megan A. Jamison, Timothy F. Massachusetts Institute of Technology. Department of Chemistry Jamison, Timothy F. Foley, Megan A. Jamison, Timothy F. A rapid carboxylic acid-promoted lactone aminolysis is reported. A number of carboxylic acids were found to promote this amide bond-forming transformation, with aliphatic acids being the most efficient. This reaction is an equilibrium process (K[subscript eq] ≈ 1.8), and mechanistic investigations are consistent with mediation of a kinetically important proton-transfer step by the carboxylate, i.e., the conjugate base of the acid employed. Novartis-MIT Center for Continuous Manufacturing 2013-01-17T16:28:32Z 2013-01-17T16:28:32Z 2010-08 Article http://purl.org/eprint/type/JournalArticle 1083-6160 1520-586X http://hdl.handle.net/1721.1/76282 Foley, Megan A., and Timothy F. Jamison. “Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis.” Organic Process Research & Development 14.5 (2010): 1177–1181. https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/10.1021/op1001269 Organic Process Research & Development Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) Prof. Jamison via Erja Kajosalo |
| spellingShingle | Foley, Megan A. Jamison, Timothy F. Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis |
| title | Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis |
| title_full | Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis |
| title_fullStr | Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis |
| title_full_unstemmed | Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis |
| title_short | Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis |
| title_sort | amide bond formation via reversible carboxylic acid promoted lactone aminolysis |
| url | http://hdl.handle.net/1721.1/76282 https://orcid.org/0000-0002-8601-7799 |
| work_keys_str_mv | AT foleymegana amidebondformationviareversiblecarboxylicacidpromotedlactoneaminolysis AT jamisontimothyf amidebondformationviareversiblecarboxylicacidpromotedlactoneaminolysis |