Indium(I) iodide promoted cleavage of diphenyl diselenide and disulfide and subsequent palladium(0)-catalyzed condensation with vinylic bromides. A simple one-pot synthesis of vinylic selenides and sulfides.
Brindaban C Ranu, Kalicharan Chattopadhyay, Subhash Banerjee
文献索引:J. Org. Chem. 71 (1) , 423-425, (2006)
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摘要
[reaction: see text] Diphenyl diselenide (and disulfide) undergo facile reaction with indium(I) iodide and the corresponding intermediate complex condenses in situ with a variety of substituted vinyl bromides in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)4] in THF at room temperature to produce vinylic selenides and sulfides in good yields. The conversion of (E)-vinyl bromides is remarkably stereoselective giving (E)-vinyl selenides (and sulpfides) whereas the stereoselectivity in reaction of (Z)-vinyl bromides is not very good.
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