Silver-mediated activation of terminal alkynes: A strategy to construct bis-ethynynl selenides and tellurides
Readily available selenium powder was chosen as an ideal selenium source to construct a series of bis(arylethynyl) selenium compounds in moderate to excellent yields through the activation of terminal alkyne C–H bond mediated by AgF. The reaction has the advantages of easy operation, good substrate scope and high atom economy. In addition, tellurium powder was also successfully applied to this system for the construction of bis(arylethynyl) tellurides under identical conditions.
Synthesis of bis(arylethynyl) selenides by one-pot protocol
An efficient method without using terminal arylacetylenes as substrates for the synthesis of bis(arylethynyl) selenides 1 (Ar≡C≡C-Se-C≡C-Ar) was described, and a series of compounds 1a-1m have been obtained by a one-pot three-step strategy from the corresponding bis(arylethanonyl) selenides. The mechanism was identified through trapping and characterization of a key intermediate 2a, and an elimination using it directly. The results from experiments indicated that the reaction procedure involves the formation of the enol phosphate and a subsequent base-induced elimination.
ACETYLENIC SELENIDES AND TELLURIDES FROM 1-BROMO, 2-PHENYL ETHYNE
Acetylenic selenides and tellurides were prepared in good yields by nucleophilic substitution at acetylenic carbon by reaction of selenolate and tellurolate anions with 1-bromo, 2-phenyl ethyne.
Dabdoub, Miguel J.,Comasseto, Joao V.
p. 1979 - 1984
(2007/10/02)
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