標題: Bromine-Radical-Mediated Synthesis of -Functionalized ,- and ,epsilon-Unsaturated Ketones via C-H Functionalization of Aldehydes
作者: Kippo, Takashi
Kimura, Yuki
Ueda, Mitsuhiro
Fukuyama, Takahide
Ryu, Ilhyong
應用化學系
Department of Applied Chemistry
關鍵字: bromine radical;S(H)2 ' reaction;beta,gamma-unsaturated ketones;delta,epsilon-unsaturated ketones;three-component reaction
公開日期: 1-九月-2017
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 beta,gamma-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 delta,epsilon-unsaturated ketones.
URI: http://dx.doi.org/10.1055/s-0036-1588494
http://hdl.handle.net/11536/145947
ISSN: 0936-5214
DOI: 10.1055/s-0036-1588494
期刊: SYNLETT
Volume: 28
起始頁: 1733
結束頁: 1737
顯示於類別:期刊論文