TY - JOUR
T1 - Bromine-Radical-Mediated Synthesis of β-Functionalized β,γ- and δ,ϵ-Unsaturated Ketones via C-H Functionalization of Aldehydes
AU - Kippo, Takashi
AU - Kimura, Yuki
AU - Ueda, Mitsuhiro
AU - Fukuyama, Takahide
AU - Ryu, Ilhyong
N1 - Publisher Copyright:
© 2017 Georg Thieme Verlag KG Stuttgart · New York.
PY - 2017/9/1
Y1 - 2017/9/1
N2 - 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.
AB - 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.
KW - SH2′ reaction
KW - bromine radical
KW - three-component reaction
KW - β,γ-unsaturated ketones
KW - δ,ϵ-unsaturated ketones
UR - http://www.scopus.com/inward/record.url?scp=85021847552&partnerID=8YFLogxK
U2 - 10.1055/s-0036-1588494
DO - 10.1055/s-0036-1588494
M3 - Article
AN - SCOPUS:85021847552
SN - 0936-5214
VL - 28
SP - 1733
EP - 1737
JO - Synlett
JF - Synlett
IS - 14
ER -