Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 16, Pages 5568-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja100651t
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Funding
- MEXT [18105004, 20038014]
- Global COE Program for Chemistry Innovation
- Japan Society for the Promotion of Science for Young Scientists [PE09025, 21.8684]
- Grants-in-Aid for Scientific Research [20038014] Funding Source: KAKEN
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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.
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