Synthesis of (E)-3-Aryl-7-methylocta-2,6-dienoic Acid via Stereoselective Mizoroki-Heck Arylation of (E)-7-Methylocta-2,6-dienoic

doi:10.6023/cjoc201809018

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1129-1135.DOI: 10.6023/cjoc201809018 Previous Articles Next Articles

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通过(E)-7-甲基-2,6-辛二烯酸的立体选择性Mizoroki-Heck芳基化反应合成(E)-3-芳基-7-甲基-2,6-辛二烯酸

王卫伟, 赵宇, 刘鑫磊, 耿瑞, 王明安

中国农业大学应用化学系北京 100193

收稿日期:2018-09-12 修回日期:2018-10-18 发布日期:2018-12-05
通讯作者: 王明安 E-mail:wangma@cau.edu.cn
基金资助:
国家自然科学基金（No.21772229）资助项目.

Synthesis of (E)-3-Aryl-7-methylocta-2,6-dienoic Acid via Stereoselective Mizoroki-Heck Arylation of (E)-7-Methylocta-2,6-dienoic

Acid Wang Weiwei, Zhao Yu, Liu Xinlei, Geng Rui, Wang Mingan

Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received:2018-09-12 Revised:2018-10-18 Published:2018-12-05
Contact: 10.6023/cjoc201809018 E-mail:wangma@cau.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No.21772229).

1. Synthesis of (E)-3-Aryl-7-methylocta-2,6-dienoic Acid via Stereoselective Mizoroki-Heck Arylation of (E)-7-Methylocta-2,6-dienoic.PDF(979KB)

Abstract

Stereoselective Mizoroki-Heck arylation of (E)-7-methylocta-2,6-dienoic acid with aryl iodide catalyzed by Pd(OAc)₂ and P(o-MeC₆H₄)₃ was optimized, and the yields were improved under the condition of excess Et₃N both as the base and solvent with reduced amount of catalysts. Twenty (E)-3-aryl-7-methylocta-2,6-dienoic acids were directly synthesized via Mizoroki-Heck arylation in 37%~68% isolated yields at reflux temperature. Their structures were characterized by IR, ¹H, ¹³C NMR, HR-ESI-MS data and X-ray diffraction.

Key words: (E)-3-aryl-7-methylocta-2,6-dienoic acid, Mizoroki-Heck arylation, configuration, synthesis

Cite this article

Acid Wang Weiwei, Zhao Yu, Liu Xinlei, Geng Rui, Wang Mingan. Synthesis of (E)-3-Aryl-7-methylocta-2,6-dienoic Acid via Stereoselective Mizoroki-Heck Arylation of (E)-7-Methylocta-2,6-dienoic[J]. Chin. J. Org. Chem., 2019, 39(4): 1129-1135.

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通过(E)-7-甲基-2,6-辛二烯酸的立体选择性Mizoroki-Heck芳基化反应合成(E)-3-芳基-7-甲基-2,6-辛二烯酸

Synthesis of (E)-3-Aryl-7-methylocta-2,6-dienoic Acid via Stereoselective Mizoroki-Heck Arylation of (E)-7-Methylocta-2,6-dienoic

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