Alkyne carbonylation by radicals: Tin-radical-catalyzed synthesis of α-methylene amides from 1-alkynes, carbon monoxide, and amines

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Abstract

A convergent synthesis of α-methylene amides exploits a hybrid radical/ionic concept in which radical carbonylation of alkynes is followed by ionic trapping of the resulting carbonyl-containing radical species with amines (see scheme). The reaction of substituted terminal alkynes with pressurized CO, Bu3SnH, and 2,2′-azobis-isobutyronitrile in the presence of a large excess of amines gave good yields of the corresponding α-methylene amides. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Uenoyama, Y., Fukuyama, T., Nobuta, O., Matsubara, H., & Ryu, I. (2005). Alkyne carbonylation by radicals: Tin-radical-catalyzed synthesis of α-methylene amides from 1-alkynes, carbon monoxide, and amines. Angewandte Chemie - International Edition, 44(7), 1075–1078. https://doi.org/10.1002/anie.200461954

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