Stereospecific and chemoselective copper-catalyzed deaminative silylation of benzylic ammonium triflates
| dc.contributor.author | Scharfbier, Jonas | |
| dc.contributor.author | Gross, Benjamin M. | |
| dc.contributor.author | Oestreich, Martin | |
| dc.date.accessioned | 2020-02-13T13:47:02Z | |
| dc.date.available | 2020-02-13T13:47:02Z | |
| dc.date.issued | 2019-12-04 | |
| dc.description.abstract | A method for the synthesis of benzylsilanes starting from the corresponding ammonium triflates is reported. Silyl boronic esters are employed as silicon pronucleophiles, and the reaction is catalyzed by copper(I) salts. Enantioenriched benzylic ammonium salts react stereospecifically through an SN2‐type displacement of the ammonium group to afford α‐chiral silanes with inversion of the configuration. A cyclopropyl‐substituted substrate does not undergo ring opening, thus suggesting an ionic reaction mechanism with no benzyl radical intermediate. | en |
| dc.description.sponsorship | DFG, 388910461, Ionische und radikalische Kreuzkupplungen zur Kohlenstoff‒Silicium-Bindungsknüpfung | en |
| dc.description.sponsorship | TU Berlin, Open-Access-Mittel - 2019 | en |
| dc.identifier.eissn | 1521-3773 | |
| dc.identifier.issn | 1433-7851 | |
| dc.identifier.uri | https://depositonce.tu-berlin.de/handle/11303/10752 | |
| dc.identifier.uri | http://dx.doi.org/10.14279/depositonce-9647 | |
| dc.language.iso | en | |
| dc.rights.uri | https://creativecommons.org/licenses/by-nc/4.0/ | |
| dc.subject.ddc | 540 Chemie und zugeordnete Wissenschaften | en |
| dc.subject.other | copper | en |
| dc.subject.other | nucleophilic substitution | en |
| dc.subject.other | silanes | en |
| dc.subject.other | stereospecificity | en |
| dc.subject.other | transmetalation | en |
| dc.title | Stereospecific and chemoselective copper-catalyzed deaminative silylation of benzylic ammonium triflates | en |
| dc.type | Article | en |
| dc.type.version | publishedVersion | en |
| dcterms.bibliographicCitation.doi | 10.1002/anie.201912490 | |
| dcterms.bibliographicCitation.issue | 4 | |
| dcterms.bibliographicCitation.journaltitle | Angewandte Chemie International Edition | en |
| dcterms.bibliographicCitation.originalpublishername | Wiley | en |
| dcterms.bibliographicCitation.originalpublisherplace | Weinheim | en |
| dcterms.bibliographicCitation.pageend | 1580 | |
| dcterms.bibliographicCitation.pagestart | 1577 | |
| dcterms.bibliographicCitation.volume | 59 | |
| tub.accessrights.dnb | free | |
| tub.affiliation | Fak. 2 Mathematik und Naturwissenschaften::Inst. Chemie::FG Organische Chemie / Synthese und Katalyse | de |
| tub.affiliation.faculty | Fak. 2 Mathematik und Naturwissenschaften | de |
| tub.affiliation.group | FG Organische Chemie / Synthese und Katalyse | de |
| tub.affiliation.institute | Inst. Chemie | de |
| tub.publisher.universityorinstitution | Technische Universität Berlin | de |
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