期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 2, 页码 238-242出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001472
关键词
Alkynes; C-C coupling; Copper; Multicomponent reactions; Palladium
资金
- Merck Serono KGaA, Darmstadt
Sonogashira coupling and the catalytic Glaser coupling are both catalyzed by the Pd-Cu complex couple and can be concatenated to a consecutive sequentially Pd/Cu-catalyzed process in a one-pot fashion, and air oxygen serves as the only oxidant in the second step. In a pseudo-four-component synthesis, a broad variety of symmetrically substituted 1,4-bis(hetero)aryl-1,3-butadiynes are obtained in good to excellent yields. Interestingly, the presence of iodide ions has been found to be advantageous over other halides to trigger the Pd/Cu-catalyzed Glaser step, and Pd and Cu species, as well as triethylamine as a base, are prerequisite for both couplings, which proceed with higher efficiency if performed in a one-pot sequence.
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