| dc.contributor.author | Li, Gen | |
| dc.contributor.author | Qin, Ziyang | |
| dc.contributor.author | Radosevich, Alexander T | |
| dc.date.accessioned | 2022-03-16T17:10:53Z | |
| dc.date.available | 2022-03-16T17:10:53Z | |
| dc.date.issued | 2020 | |
| dc.identifier.uri | https://hdl.handle.net/1721.1/141228 | |
| dc.description.abstract | Copyright © 2020 American Chemical Society. The direct reductive N-arylation of nitromethane by organophosphorus-catalyzed reductive C-N coupling with arylboronic acid derivatives is reported. This method operates by the action of a small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) together with a mild terminal reductant hydrosilane to drive the selective installation of the methylamino group to (hetero)aromatic boronic acids and esters. This method also provides for a unified synthetic approach to isotopically labeled N-methylanilines from various stable isotopologues of nitromethane (i.e., CD3NO2, CH315NO2, and 13CH3NO2), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group. | en_US |
| dc.language.iso | en | |
| dc.publisher | American Chemical Society (ACS) | en_US |
| dc.relation.isversionof | 10.1021/JACS.0C08035 | en_US |
| dc.rights | Creative Commons Attribution-Noncommercial-Share Alike | en_US |
| dc.rights.uri | http://creativecommons.org/licenses/by-nc-sa/4.0/ | en_US |
| dc.source | PMC | en_US |
| dc.title | P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C–N Coupling with Nitromethane as a Methylamine Surrogate | en_US |
| dc.type | Article | en_US |
| dc.identifier.citation | Li, Gen, Qin, Ziyang and Radosevich, Alexander T. 2020. "P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C–N Coupling with Nitromethane as a Methylamine Surrogate." Journal of the American Chemical Society, 142 (38). | |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | |
| dc.relation.journal | Journal of the American Chemical Society | en_US |
| dc.eprint.version | Author's final manuscript | en_US |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
| eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
| dc.date.updated | 2022-03-16T17:06:14Z | |
| dspace.orderedauthors | Li, G; Qin, Z; Radosevich, AT | en_US |
| dspace.date.submission | 2022-03-16T17:06:15Z | |
| mit.journal.volume | 142 | en_US |
| mit.journal.issue | 38 | en_US |
| mit.license | OPEN_ACCESS_POLICY | |
| mit.metadata.status | Authority Work and Publication Information Needed | en_US |
