Oxidative coupling of alkynes mediated by nitroxyl radicals under Sonogashira conditions and Pd-free catalytic approach to stable radicals of 3-imidazoline family with triple bonds |
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| Authors: | Sergei F Vasilevsky Olga L Krivenko |
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| Institution: | a Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Science, 630090 Novosibirsk, Russian Federation
b Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, United States |
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| Abstract: | In the presence of Pd catalyst, 3-imidazoline nitroxyl radicals promote oxidative coupling (dimerization) of terminal alkynes even in the absence of Cu(II) additives. On the other hand, the Pd-free CuI-PPh3-K2CO3-DMF catalytic system leads to the efficient cross-coupling of 1-hydroxy-4-2-(p-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide with terminal aryl- and hetarylacetylenes with the formation of 4-2-(aryl/hetarylethynyl)phenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyls in 70-75% yields. |
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| Keywords: | Cross-coupling Aryl- and hetarylacetylenes 3-Imidazoline-nitroxyles Oxidative coupling Stable radicals |
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