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Hu, Shicheng ; Massachusetts Institute of Technology,2024.
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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.
Purchased from AmBeed: 18820-82-1 ; 29263-94-3 ; 775-12-2 ; 33530-51-7
CAS No. : | 18820-82-1 | MDL No. : | MFCD00012801 |
Formula : | C5H6BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BBFCIBZLAVOLCF-UHFFFAOYSA-N |
M.W : | 160.01 | Pubchem ID : | 87810 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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