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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. : | 29263-94-3 | MDL No. : | MFCD00009125 |
Formula : | C8H13BrO4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | CSLQAXTUGPUBCW-UHFFFAOYSA-N |
M.W : | 253.09 | Pubchem ID : | 94944 |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3265 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium fluoride; In N,N-dimethyl-formamide; at 60℃; for 4h;Cooling with ice; | To an ice-cold solution of <strong>[39903-01-0]2-amino-5-bromopyridin-3-ol</strong> (1 g, 5.29 mmol) in DMF (10 mL) was added KF (0.77 g, 13.23 mmol) followed by addition of diethyl 2-bromo-2-methylmalonate (1 mL, 5.29 mmol) and the mixture heated up to 60° C. for 4 h. After completion (by TLC), the reaction was cooled, quenched with water and extracted with EtOAc (3.x.100 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain the desired product as an off-white solid (1 g, 60percent). |
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