Coupling and cycloaddition of ynamides: homo- and Negishi coupling of tosylynamides and intramolecular [4+2] cycloaddition of N-(o-ethynyl)phenyl ynamides and arylynamides |
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Authors: | Marí a Fernanda Martí nez-Esperó n |
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Affiliation: | Departamento de Química Orgánica y Unidad Asociada al CSIC, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain |
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Abstract: | N,N′-aryl- and N,N′-alkyl-buta-1,3-diyne-1,4-ditosylamides have been synthesized for the first time, in good to excellent yields, by copper-catalyzed dimerization of the corresponding N-aryl or N-alkyl tosylynamides. Negishi coupling of N-ethynylzinc tosylamides derivatives with (hetero)aryl iodides in the presence of Pd2dba3 and triphenylphosphine affords N-aryl and N-alkyl arylynamides in yields of up to 90%. Intramolecular [4+2] cycloaddition reactions of N-ethynylphenyl ynamides and arylynamides allow the synthesis of carbazoles and benzannulated and heteroannulated carbazoles in moderate-to-good yields. |
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Keywords: | Alkynylation Carbazoles Coupling Cycloaddition Ynamides |
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