| dc.contributor.author | Lecomte, Morgan | |
| dc.contributor.author | Lipshultz, Jeffrey M. | |
| dc.contributor.author | Kim-Lee, Shin-Ho | |
| dc.contributor.author | Li, Gen | |
| dc.contributor.author | Radosevich, Alexander T. | |
| dc.date.accessioned | 2020-04-27T17:26:52Z | |
| dc.date.available | 2020-04-27T17:26:52Z | |
| dc.date.issued | 2019-07-25 | |
| dc.identifier.issn | 0002-7863 | |
| dc.identifier.issn | 1520-5126 | |
| dc.identifier.uri | https://hdl.handle.net/1721.1/124882 | |
| dc.description.abstract | 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 | en_US |
| dc.description.sponsorship | NIH NIGMS (grant no. GM114547) | en_US |
| dc.publisher | American Chemical Society (ACS) | en_US |
| dc.relation.isversionof | 10.1021/jacs.9b06277 | en_US |
| dc.rights | Creative Commons Attribution-NonCommercial-NoDerivs License | en_US |
| dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | en_US |
| dc.source | ACS | en_US |
| dc.subject | Colloid and Surface Chemistry | en_US |
| dc.subject | Biochemistry | en_US |
| dc.subject | General Chemistry | en_US |
| dc.subject | Catalysis | en_US |
| dc.title | Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation | en_US |
| dc.type | Article | en_US |
| dc.identifier.citation | 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) | en_US |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
| dc.relation.journal | Journal of the American Chemical Society | en_US |
| dc.eprint.version | Final published version | en_US |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
| eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
| dspace.date.submission | 2019-11-25T19:46:55Z | |
| mit.journal.volume | 141 | en_US |
| mit.journal.issue | 32 | en_US |
| mit.metadata.status | Complete | |
