Bromine-Radical-Mediated Synthesis of β-Functionalized β,γ- and δ,ϵ-Unsaturated Ketones via C-H Functionalization of Aldehydes

Takashi Kippo, Yuki Kimura, Mitsuhiro Ueda, Takahide Fukuyama, Ilhyong Ryu*

*此作品的通信作者

研究成果: Article同行評審

11 引文 斯高帕斯(Scopus)

摘要

The bromine-radical-mediated allylation reaction of aldehydes was studied. In the presence of V-65 as radical initiator, the reaction of aldehydes with allyl bromides gave β,γ-unsaturated ketones in good yields (13 examples, 45-84%). The reaction is triggered by hydrogen abstraction from the aldehyde by bromine radical to form an acyl radical, which undergoes an S H 2′-type addition-elimination reaction with allyl bromides to give coupling products with liberation of bromine radical. Three-component coupling reactions comprising aldehydes, electron-deficient alkenes, and methallyl bromide also proceeded to give δ,ϵ-unsaturated ketones.

原文English
頁(從 - 到)1733-1737
頁數5
期刊Synlett
28
發行號14
DOIs
出版狀態Published - 1 9月 2017

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