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Journal of Zhejiang University SCIENCE B 2006 Vol.7 No.3 P.193-197

http://doi.org/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


Author(s):  Liu Yun-Kui, Zheng Hui, Xu Dan-Qian, Xu Zhen-Yuan, Zhang Yong-Min

Affiliation(s):  State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China; more

Corresponding email(s):   CHRC@mail.hz.zj.cn, yminzhang@mail.hz.zj.cn

Key Words:  Baylis-Hillman adduct, (Z)-allyl iodide, Samarium triiodide, Ionic liquid


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[J]. Journal of Zhejiang University Science B, 2006, 7(3): 193-197.

@article{title="Remarkable rate acceleration of SmI3-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid: facile synthesis of (Z)-allyl iodides",
author="Liu Yun-Kui, Zheng Hui, Xu Dan-Qian, Xu Zhen-Yuan, Zhang Yong-Min",
journal="Journal of Zhejiang University Science B",
volume="7",
number="3",
pages="193-197",
year="2006",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2006.B0193"
}

%0 Journal Article
%T Remarkable rate acceleration of SmI3-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid: facile synthesis of (Z)-allyl iodides
%A Liu Yun-Kui
%A Zheng Hui
%A Xu Dan-Qian
%A Xu Zhen-Yuan
%A Zhang Yong-Min
%J Journal of Zhejiang University SCIENCE B
%V 7
%N 3
%P 193-197
%@ 1673-1581
%D 2006
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2006.B0193

TY - JOUR
T1 - Remarkable rate acceleration of SmI3-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid: facile synthesis of (Z)-allyl iodides
A1 - Liu Yun-Kui
A1 - Zheng Hui
A1 - Xu Dan-Qian
A1 - Xu Zhen-Yuan
A1 - Zhang Yong-Min
J0 - Journal of Zhejiang University Science B
VL - 7
IS - 3
SP - 193
EP - 197
%@ 1673-1581
Y1 - 2006
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.2006.B0193


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.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

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