| Remarkable rate acceleration of SmI3-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid： facile synthesis of （Z）-allyl iodides |
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| 作者姓名： | Liu YK Zheng H Xu DQ Xu ZY Zhang YM |
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| 作者单位： | State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China |
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| 基金项目： | Project （No. 2004C21032） supported by the Key Technology R ＆ D Program of Zhej iang Province, China |
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| 摘 要： | Stereoselective transformation of Baylis-Hillman acetates I into corresponding （Z）-allyl iodides 2 has been achieved by treatment of I with samarium triiodide in THF. Remarkable rate acceleration of samarium triiodide-mediated iodination of 1 was found when ionic liquid 1-n-butyl-3-methyl-imidazolium tetrafluroborate （bmim]BF4） was used as reaction media in stead of THF. This novel approach proceeds readily at 50 ℃ within a few minutes to afford （Z）-allyl iodides 2 in excellent yields. A mechanism involving stereoselective iodination of the acetates of Baylis-Hillman adducts by samarium triiodide is described, in which a six-membered ring transition state played a key role in the stereoselective formation of 2.
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| 关 键 词： | 碘 吸收 山区居民 三碘化钐 离子液 |
| 收稿时间： | 2005-11-21 |
| 修稿时间： | 2005-12-21 |
Remarkable rate acceleration of SmI3-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid: facile synthesis of (Z)-allyl iodides |
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| Liu YK,Zheng H,Xu DQ,Xu ZY,Zhang YM.Remarkable rate acceleration of SmI3-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid: facile synthesis of (Z)-allyl iodides[J].Journal of Zhejiang University Science,2006,7(3):193-197. |
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| Authors: | Yun-kui Liu Hui Zheng Dan-qian Xu Zhen-yuan Xu Yong-min Zhang |
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| Institution: | (1) State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, China;(2) Department of Chemistry, Zhejiang University, Hangzhou, 310028, China |
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| Abstract: | Stereoselective transformation of Baylis-Hillman acetates 1 into corresponding (Z)-allyl iodides 2 has been achieved by treatment of 1 with samarium triiodide in THF. Remarkable rate acceleration of samarium triiodide-mediated iodination of 1 was found when ionic liquid 1-n-butyl-3-methyl-imidazolium tetrafluroborate (bmim]BF4) was used as reaction media in stead of THF. This novel approach proceeds readily at 50 °C within a few minutes to afford
(Z)-allyl iodides 2 in excellent yields. A mechanism involving stereoselective iodination of the acetates of Baylis-Hillman adducts by samarium
triiodide is described, in which a six-membered ring transition state played a key role in the stereoselective formation of
2.
Project (No. 2004C21032) supported by the Key Technology R & D Program of Zhejiang Province, China |
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| Keywords: | Baylis-Hillman adduct (Z)-allyl iodide Samarium triiodide Ionic liquid |
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