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

Abstract

[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.