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Titanium(IV) chloride and quaternary ammonium salt promoted baylis-hillman reaction
其他题名四氯化钛和季胺盐促进的Baylis-Hillman 反应
Shi M(施敏); Feng YS(冯言枢); Shi M(施敏)
2001
发表期刊J. Org. Chem.
卷号66期号:2页码:406-411
摘要The Baylis-Hillman reaction of aldehyds with α, β-unsaturated ketones can be drastically affected by the reaction temperature and lewis bases. When the reaction was carried out at -78℃ using catalytic amounts of quaternary ammonium salts (R^4N+X-,X=Cl, Br, I) as lewis bases, in the presence of titanium (IV) chloride, the chlorinated aldol adduct 1 was obtained as the major product. Quaternary ammonium bromides and iodides (R^4N+X-,X=Cl, Br, I) have higher catalytic activity than corresponding chlorides (R^4N+Cl-). Quaternary ammonium fluorides (R^4N+F-) do not have activity at all. The amounts of Lewis acid and quaternary ammonium salts used affect the reaction rate and product. A plausible reaction mechanism is proposed. If the reaction was carried out at rate and product. A plausible reaction mechanism is proposed. If the reaction was carried out at room temperature (about 20℃ ) in the presence of titanium (IV) chloride and quaternary ammonium salts (R^4N+X-,X=Cl, Br, I) , the elimination product 3, derived from 1, was formed as the major product.
学科领域金属有机化学
部门归属中国科学院上海有机化学研究所金属有机化学开放实验室
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收录类别SCI
语种英语
WOS记录号WOS:000166560600007
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文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/9754
专题金属有机化学国家重点实验室
通讯作者Shi M(施敏)
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Shi M,Feng YS,Shi M. Titanium(IV) chloride and quaternary ammonium salt promoted baylis-hillman reaction[J]. J. Org. Chem.,2001,66(2):406-411.
APA Shi M,Feng YS,&施敏.(2001).Titanium(IV) chloride and quaternary ammonium salt promoted baylis-hillman reaction.J. Org. Chem.,66(2),406-411.
MLA Shi M,et al."Titanium(IV) chloride and quaternary ammonium salt promoted baylis-hillman reaction".J. Org. Chem. 66.2(2001):406-411.
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