Iron-catalyzed C-C bond formation at alpha-position of aliphatic amines via C-H bond activation through 1,5-hydrogen transfer.
Iron-catalyzed C-C bond formation at alpha-position of aliphatic amines via C-H bond activation through 1,5-hydrogen transfer.
复制标题
DOI：
10.1021/ja100651t
复制
发表时间：
2010-04
影响因子：
15
通讯作者：
N. Yoshikai;Adam Mieczkowski;A. Matsumoto;L. Ilies;E. Nakamura
中科院分区：
文献类型：
--
作者：
N. Yoshikai;Adam Mieczkowski;A. Matsumoto;L. Ilies;E. Nakamura
通过有机铁发生的C-C键形成反应有时表现出类似自由基的特征。N-（2-碘苯基甲基）二烷基胺与格氏试剂或二有机锌试剂在催化量的铁（acac）(3)存在下的反应，可得到胺基旁sp(3) C-H键的芳化、烯化或烷基化的产物，收率很高。包括标记实验在内的机制研究表明，该反应涉及自由基易位，这是由去除碘化基团形成自由基样物质引发的。
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 sp(3) 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.