Coupling and cycloaddition of ynamides: homo-and Negishi coupling of tosylynamides and intramolecular [4+ 2] cycloaddition of N-(o-ethynyl) phenyl ynamides and …

MF Martínez-Esperón, D Rodríguez, L Castedo, C Saá

Index: Martinez-Esperon, Maria Fernanda; Rodriguez, David; Castedo, Luis; Saa, Carlos Tetrahedron, 2006 , vol. 62, # 16 p. 3843 - 3855

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Citation Number: 33

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%. ...