How to make C-N bonds using boronic acids and their derivatives without transition metals
| dc.contributor.author | García Csaky, Aurelio | |
| dc.contributor.author | Roscales García, Silvia | |
| dc.date.accessioned | 2025-01-09T14:48:18Z | |
| dc.date.available | 2025-01-09T14:48:18Z | |
| dc.date.issued | 2020-07 | |
| dc.description | Key learning points (1) Formation of tetrahedral boronates induces a nucleophilic activation of the carbon backbone of boronic acids and their derivatives (boronic acids, boronate esters, or potassium organotrifluoroborates). (2) N–B coordination of a variety of N-LG reagents (LG = Leaving Group) followed by 1,2-C(B–N)-shift triggers C–N bond formation in the absence of transitionmetals. (3) Deoxygenation of nitro and nitroso groups turns them into useful nitrogen electrophiles for amine formation. (4) Acylboron compounds react with N-LG reagents (LG = leaving group) through their carbonyl group to form hemiaminals that evolve to amides. | |
| dc.description.abstract | This tutorial review describes recent developments in carbon–nitrogen bond-forming reactions (amination, amidation, nitration and nitrosation) that involve the use of boronic acids and some of their derivatives as carbon-nucleophiles in the absence of transition-metals. Issues pertaining to reagents and mechanisms are discussed. | |
| dc.description.department | Depto. de Química Orgánica | |
| dc.description.faculty | Instituto Pluridisciplinar (IP) | |
| dc.description.refereed | TRUE | |
| dc.description.sponsorship | Ministerio de Ciencia, Innovacio´n y Universidades | |
| dc.description.status | pub | |
| dc.identifier.citation | Chem. Soc. Rev., 2020,49, 5159-5177 | |
| dc.identifier.doi | 10.1039/c9cs00735k | |
| dc.identifier.officialurl | https://pubs.rsc.org/en/content/articlelanding/2020/cs/c9cs00735k | |
| dc.identifier.uri | https://hdl.handle.net/20.500.14352/113549 | |
| dc.journal.title | Chemical Society Reviews | |
| dc.language.iso | eng | |
| dc.page.final | 5177 | |
| dc.page.initial | 5159 | |
| dc.publisher | Royal Society of Chemistry | |
| dc.relation.projectID | RTI2018-096520-B-I00 | |
| dc.rights.accessRights | restricted access | |
| dc.subject.ucm | Ciencias | |
| dc.subject.unesco | 23 Química | |
| dc.title | How to make C-N bonds using boronic acids and their derivatives without transition metals | |
| dc.title.alternative | Cómo hacer enlaces C-N usando ácidos borónicos y sus derivados sin usar metales de transición | |
| dc.type | journal article | |
| dc.type.hasVersion | AM | |
| dc.volume.number | 49 | |
| dspace.entity.type | Publication | |
| relation.isAuthorOfPublication | 20fb9911-4424-43a0-ad98-890ff7a6dacd | |
| relation.isAuthorOfPublication | ef4f93d7-a007-4514-9055-f8ba8c41138d | |
| relation.isAuthorOfPublication.latestForDiscovery | 20fb9911-4424-43a0-ad98-890ff7a6dacd |
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