Iron-catalyzed C-C bond formation at alpha-position of aliphatic amines via C-H bond activation through 1,5-hydrogen transfer.
摘要:
C−C bond formation reactions that take place through organoiron species sometimes exhibit radical-like character. The reaction of N-(2-iodophenylmethyl)dialkylamine with a Grignard or diorganozinc reagent in the presence of a catalytic amount of Fe(acac)3 gives the product resulting from arylation, alkenylation, or alkylation of the sp3 C−H bond next to the amine group in good to excellent yield. Mechanistic studies including labeling experiments indicate that the reaction involves radical translocation triggered by the formation of a radical-like species by removal of the iodide group.
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DOI:
10.1021/ja100651t
被引量:
年份:
2010
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