| dc.contributor.advisor | Radosevich, Alexander T. | |
| dc.contributor.author | Hu, Shicheng | |
| dc.date.accessioned | 2024-12-02T21:15:20Z | |
| dc.date.available | 2024-12-02T21:15:20Z | |
| dc.date.issued | 2024-05 | |
| dc.date.submitted | 2024-11-18T19:27:25.107Z | |
| dc.identifier.uri | https://hdl.handle.net/1721.1/157726 | |
| dc.description.abstract | A catalytic method for the direct electrophilic cyanation of C(sp²)–H nucleophiles with sodium cyanate (NaOCN) is reported. Mechanistic experiments show that under solid-liquid phase transfer, an inorganic cyanate is activated by halide displacement on a halophosphonium. Redox catalysis is enabled by the usage of a strained phosphine (phosphetane) so that catalyst turnover from phosphine oxide to phosphine can be easily achieved by the usage of a terminal hydrosilane reductant. These results demonstrate the feasibility of deoxyfunctionalization of insoluble inorganic salts by Pᴵᴵᴵ/Pⱽ=O catalyzed phase transfer activation, as exemplified by C(sp²)–H cyanation with NaOCN as the “CN⁺” source. | |
| dc.publisher | Massachusetts Institute of Technology | |
| dc.rights | In Copyright - Educational Use Permitted | |
| dc.rights | Copyright retained by author(s) | |
| dc.rights.uri | https://rightsstatements.org/page/InC-EDU/1.0/ | |
| dc.title | Electrophilic C(sp²)–H Cyanation with Inorganic Cyanate (OCN⁻) by Pᴵᴵᴵ/Pⱽ=O-Catalyzed Phase Transfer Activation | |
| dc.type | Thesis | |
| dc.description.degree | S.B. | |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | |
| mit.thesis.degree | Bachelor | |
| thesis.degree.name | Bachelor of Science in Chemistry | |
