10.1002/adsc.201800985
Advanced Synthesis & Catalysis
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Scheme 5. Plausible mechanistic pathway.
In conclusion, we have developed a convenient
Ce(IV)-promoted phosphinoylation-nitratation of
alkenes under mild conditions. CAN was used as a
cheap P(O)-radical initiator providing an important
supplement to phosphorus radical chemistry.
Furthermore, the highly effective utilization of CAN
conferred this process with both high material and
atom economy. This method can be easily adapted to
large-scale preparations. Additional studies on the
reaction mechanism and synthetic applications are
underway in our laboratory.
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Experimental Section
To a Schlenk tube was added diphenylphosphine oxide 2a
(0.2 mmol), (NH4)2Ce(NO3)6 (0.4 mmol) before being
charged with argon three times. Then, anhydrous 1, 4-
dioxane (2.0 mL) and styrene 1a (0.5 mmol) were added
o
via syringe. The mixture was allowed to stir at 40 C in an
oil bath overnight. At the completion of the reaction, the
reaction mixture was cooled to room temperature, and the
solvent was removed by rotary evaporation. The resulting
residue was purified by column chromatography on silica
gel (petroleum ether/ethyl acetate = 2:1) to afford the
product 2-(diphenylphosphoryl)-1-phenylethyl nitrate 3a.
Acknowledgements
We thank the National Natural Science Foundation of China (no.
51573155), Natural Science Foundation of Shandong Province
(no. ZR2017LB007 and ZR2017BEM016) and A Project of
Shandong Province Higher Educational Science and Technology
Program (no. J18KA074) for financial support
[4] Selected recent papers on P-radical involved
difunctionalization of alkenes: a) W. Wei, J. X. Ji,
Angew. Chem., Int. Ed. 2011, 50, 9097-9099; b) T.
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