Alkyne Carbonylation by Radicals: Tin-Radical-Catalyzed Synthesis of α-Methylene Amides from 1-Alkynes, Carbon Monoxide, and Amines

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...

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Veröffentlicht in:	Angewandte Chemie International Edition 2005-02, Vol.44 (7), p.1075-1078
Hauptverfasser:	Uenoyama, Yoshitaka, Fukuyama, Takahide, Nobuta, Osamu, Matsubara, Hiroshi, Ryu, Ilhyong
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Sprache:	eng
Schlagworte:	alkynes amides carbonylation radical reactions tin
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creator	Uenoyama, Yoshitaka Fukuyama, Takahide Nobuta, Osamu Matsubara, Hiroshi Ryu, Ilhyong
description	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′‐azobisisobutyronitrile in the presence of a large excess of amines gave good yields of the corresponding α‐methylene amides.
doi_str_mv	10.1002/anie.200461954
format	Article
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subjects	alkynes amides carbonylation radical reactions tin
title	Alkyne Carbonylation by Radicals: Tin-Radical-Catalyzed Synthesis of α-Methylene Amides from 1-Alkynes, Carbon Monoxide, and Amines
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