Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 12, Pages 4543-4549Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c00237
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- JSPS KAKENHI [JP15H05839, JP17K19126, JP18H04271]
- JST CREST [JPMJCR20R1]
- Japan Society for the Promotion of Science (JSPS) [JP19J12813]
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A new method for the C-H homoallylation reaction of aromatic ketones with methylenecyclopropanes using a catalytic amount of Fe(PMe3)(4) was reported, yielding selectively ortho-homoallylated aromatic ketones through regioselective scission of the three-membered rings. The homoallylated products are suitable for further modifications, leading to functionalized 1,2-dihydronaphthalenes.
We report here a C-H homoallylation reaction of aromatic ketones with methylenecyclopropanes (MCPs) only using a catalytic amount of Fe(PMe3)(4). A variety of aromatic ketones and MCPs are applicable to the reaction to form ortho-homoallylated aromatic ketones selectively via regioselective scission of the three-membered rings. The homoallylated products are amenable to further elaborations, providing functionalized 1,2-dihydronaphthalenes.
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