Journal
ORGANIC LETTERS
Volume 19, Issue 19, Pages 5252-5255Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02526
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- Vanderbilt University
- Institute of Chemical-Biology
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A one-pot, metal-free procedure has been developed to synthesize unsymmetrical organoselenides. In the first step of the reaction, arylation of potassium selenocyanate (KSeCN) with an iodonium reagent proceeds in the absence of a metal catalyst to produce an arylselenocyanate. In the second step, treatment with sodium borohydride unmasks a second selenium nucleophile that engages an aliphatic electrophile, iodonium reagent, or glycosyl halide. The procedure represents an umpolung approach to the synthesis of aryl-selenides.
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