10.1002/adsc.201901201
Advanced Synthesis & Catalysis
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equipped with a stir bar was added benzyl phenyl selenoxide
(2.6 mg, 0.01 mmol, 0.025 equiv, from a stock solution in
4.0 ml toluene) and KN(SiMe3)2 (160 mg, 0.8 mmol, 2.0
equiv) under a nitrogen atmosphere followed by dry toluene
(4.0 mL) with the yellow and clear solution generated. The
microwave vial was sealed with a vial cap with a rubber
insert and the sealed vial was removed from the dry box.
Benzyl chloride (46 μL, 0.40 mmol, 1.0 equiv) was then
added by a syringe under nitrogen. Note that if the benzyl
halide was a solid, it was added to the reaction vial inside the
dry box before the vial sealed. The reaction mixture was
stirred for 4 hours at room temperature. After the reaction
was complete, a yellow, orange or red solution was formed,
and the sealed vial was opened to air, quenched with three
drops of deionized water and the reaction mixture was
passed through a short pad of silica gel. The silica gel was
then rinsed with ethyl acetate (10 mL). The solvent was
removed under reduced pressure. The resulting residue was
purified by flash chromatography.
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Acknowledgement
We thank the National Science Foundation (CHE-1902509
to PJW) for financial support. DJM thanks the University of
Pennsylvania for research funds. O.S.T. acknowledges
financial support from FONDECYT/Postdoctorado no
3160270.
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contains
the
supplementary
crystallographic data for this paper. These data can be obtained
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