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Journal of Zhejiang University-SCIENCE B (Biomedicine & Biotechnology)  2006, Vol. 7 Issue (3 ): 4-    DOI: 10.1631/jzus.2006.B0193
    
Remarkable rate acceleration of SmI3-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid: facile synthesis of (Z)-allyl iodides
Liu Yun-Kui, Zheng Hui, Xu Dan-Qian, Xu Zhen-Yuan, Zhang Yong-Min
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China; 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.

Key wordsBaylis-Hillman adduct      (Z)-allyl iodide      Samarium triiodide      Ionic liquid     
Received: 21 November 2005     
CLC:  O641.6  
Cite this article:

Liu Yun-Kui, Zheng Hui, Xu Dan-Qian, Xu Zhen-Yuan, Zhang Yong-Min. Remarkable rate acceleration of SmI3-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid: facile synthesis of (Z)-allyl iodides. Journal of Zhejiang University-SCIENCE B (Biomedicine & Biotechnology), 2006, 7(3 ): 4-.

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http://www.zjujournals.com/xueshu/zjus-b/10.1631/jzus.2006.B0193     OR     http://www.zjujournals.com/xueshu/zjus-b/Y2006/V7/I3 /4

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[2] Liu Yun-kui, Xu Dan-qian, Xu Zhen-yuan, Zhang Yong-min. A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides[J]. Journal of Zhejiang University-SCIENCE B (Biomedicine & Biotechnology), 2006, 7(5 ): 9-.