Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation
A method for the annulation of amines and carboxylic acids to form pharmaceutically relevant azaheterocycles via organophosphorus PIII/PV redox catalysis is reported. The method employs a phosphetane catalyst together with a mild bromenium oxidant and terminal hydrosilane reductant to drive successi...
| Main Authors: | , , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Published: |
American Chemical Society (ACS)
2020
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/1721.1/124882 |
| _version_ | 1826206948935073792 |
|---|---|
| author | Lecomte, Morgan Lipshultz, Jeffrey M. Kim-Lee, Shin-Ho Li, Gen Radosevich, Alexander T. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Lecomte, Morgan Lipshultz, Jeffrey M. Kim-Lee, Shin-Ho Li, Gen Radosevich, Alexander T. |
| author_sort | Lecomte, Morgan |
| collection | MIT |
| description | A method for the annulation of amines and carboxylic acids to form pharmaceutically relevant azaheterocycles via organophosphorus PIII/PV redox catalysis is reported. The method employs a phosphetane catalyst together with a mild bromenium oxidant and terminal hydrosilane reductant to drive successive C–N and C–C bond-forming dehydration events via the serial action of a catalytic bromophosphonium intermediate. These results demonstrate the capacity of PIII/PV redox catalysis to enable iterative redox-neutral transformations in complement to the common reductive driving force of the PIII/PV couple. ©2019 |
| first_indexed | 2024-09-23T13:41:26Z |
| format | Article |
| id | mit-1721.1/124882 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2024-09-23T13:41:26Z |
| publishDate | 2020 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1248822022-09-28T15:32:19Z Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation Lecomte, Morgan Lipshultz, Jeffrey M. Kim-Lee, Shin-Ho Li, Gen Radosevich, Alexander T. Massachusetts Institute of Technology. Department of Chemistry Colloid and Surface Chemistry Biochemistry General Chemistry Catalysis A method for the annulation of amines and carboxylic acids to form pharmaceutically relevant azaheterocycles via organophosphorus PIII/PV redox catalysis is reported. The method employs a phosphetane catalyst together with a mild bromenium oxidant and terminal hydrosilane reductant to drive successive C–N and C–C bond-forming dehydration events via the serial action of a catalytic bromophosphonium intermediate. These results demonstrate the capacity of PIII/PV redox catalysis to enable iterative redox-neutral transformations in complement to the common reductive driving force of the PIII/PV couple. ©2019 NIH NIGMS (grant no. GM114547) 2020-04-27T17:26:52Z 2020-04-27T17:26:52Z 2019-07-25 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 https://hdl.handle.net/1721.1/124882 Lecomte, Morgan, Jeffrey M. Lipshultz, Shin-Ho Kim-Lee, Gen Li, and Alexander T. Radosevich, "Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation." Journal of the American Chemical Society 141, 32 (July 2019): p. 12507-12 doi 10.1021/jacs.9b06277 ©2019 Author(s) 10.1021/jacs.9b06277 Journal of the American Chemical Society Creative Commons Attribution-NonCommercial-NoDerivs License http://creativecommons.org/licenses/by-nc-nd/4.0/ application/pdf American Chemical Society (ACS) ACS |
| spellingShingle | Colloid and Surface Chemistry Biochemistry General Chemistry Catalysis Lecomte, Morgan Lipshultz, Jeffrey M. Kim-Lee, Shin-Ho Li, Gen Radosevich, Alexander T. Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation |
| title | Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation |
| title_full | Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation |
| title_fullStr | Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation |
| title_full_unstemmed | Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation |
| title_short | Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation |
| title_sort | driving recursive dehydration by piii pv catalysis annulation of amines and carboxylic acids by sequential c n and c c bond formation |
| topic | Colloid and Surface Chemistry Biochemistry General Chemistry Catalysis |
| url | https://hdl.handle.net/1721.1/124882 |
| work_keys_str_mv | AT lecomtemorgan drivingrecursivedehydrationbypiiipvcatalysisannulationofaminesandcarboxylicacidsbysequentialcnandccbondformation AT lipshultzjeffreym drivingrecursivedehydrationbypiiipvcatalysisannulationofaminesandcarboxylicacidsbysequentialcnandccbondformation AT kimleeshinho drivingrecursivedehydrationbypiiipvcatalysisannulationofaminesandcarboxylicacidsbysequentialcnandccbondformation AT ligen drivingrecursivedehydrationbypiiipvcatalysisannulationofaminesandcarboxylicacidsbysequentialcnandccbondformation AT radosevichalexandert drivingrecursivedehydrationbypiiipvcatalysisannulationofaminesandcarboxylicacidsbysequentialcnandccbondformation |