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Reaction of Baylis-Hillman Adducts with Fluorinated Silanes
其他题名Baylis-Hillman加成物与含氟硅烷的反应
Zemtsov, Artem A.; Levin, Vitalij V.; Dilman, Alexander D.; Struchkova, Marina I.; Belyakov, Pavel A.; Tartakovsky, Vladimir A.; Hu JB(胡金波)
2010
发表期刊Eur. J. Org. Chem.
ISSN1434-193X
期号35页码:6779-6785
其他摘要Reactions of acylated Baylis–Hillman adducts bearing nitrile, ester, or ketone groups with C6F5-substituted silicon reagents MenSi(C6F5)4–n (n = 1–3) have been studied. The reactions are initiated by Bu4NOAc (5 mol-%) in MeCN or DMF under mild conditions and afford products of allylic substitution of the acetoxy group by the C6F5 carbanion in good yields. Predominant or exclusive formation of one geometrical isomer was observed in all cases (Z for nitriles, E for esters and ketones). For substrates containing carbonyl groups, nucleophilic attack of the C6F5 carbanion chemoselectively occurred at the C=C bond. Reactions of acylated Baylis–Hillman adducts with Me3SiCF3 were found to be inefficient, as the CF3 carbanion had the propensity to attack the C=O bond of substrates with ester or ketone substituents.
学科领域氟化学
部门归属俄罗斯科学院有机化学研究所; 中国科学院上海有机化学研究所
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收录类别SCI
语种英语
WOS记录号WOS:000285310700010
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被引频次:18[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/24079
专题中科院有机氟化学重点实验室
通讯作者Dilman, Alexander D.; Hu JB(胡金波)
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GB/T 7714
Zemtsov, Artem A.,Levin, Vitalij V.,Dilman, Alexander D.,et al. Reaction of Baylis-Hillman Adducts with Fluorinated Silanes[J]. Eur. J. Org. Chem.,2010(35):6779-6785.
APA Zemtsov, Artem A..,Levin, Vitalij V..,Dilman, Alexander D..,Struchkova, Marina I..,Belyakov, Pavel A..,...&胡金波.(2010).Reaction of Baylis-Hillman Adducts with Fluorinated Silanes.Eur. J. Org. Chem.(35),6779-6785.
MLA Zemtsov, Artem A.,et al."Reaction of Baylis-Hillman Adducts with Fluorinated Silanes".Eur. J. Org. Chem. .35(2010):6779-6785.
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