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Alkyne Carbonylation by Radicals: Tin‐Radical‐Catalyzed Synthesis of α‐Methylene Amides from 1‐Alkynes, Carbon Monoxide, and Amines
Author(s) -
Uenoyama Yoshitaka,
Fukuyama Takahide,
Nobuta Osamu,
Matsubara Hiroshi,
Ryu Ilhyong
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461954
Subject(s) - chemistry , carbonylation , methylene , alkyne , radical , carbon monoxide , ionic bonding , azobisisobutyronitrile , organic chemistry , catalysis , medicinal chemistry , ion , polymer , polymerization
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, Bu 3 SnH, and 2,2′‐azobisisobutyronitrile in the presence of a large excess of amines gave good yields of the corresponding α‐methylene amides.