Stereoselective synthesis of 2-iodo-1-perfluoroalkyl-2(Z)-alkenes and E or Z-4-perfluoroalkylmethyl-4-en-2-ynol via Na2S2O4-promoted radical addition reaction of perfluoroalkyl iodides with allenes and the palladium-catalyzed kinetic resolution with Sonogashira coupling reaction

被引：16
|
作者：
Ma, Zhichao [1 ]
Ma, Shengming [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China
来源：
TETRAHEDRON | 2008年 / 64卷 / 27期
关键词：
radical addition; allenes; perfluoroalkyl iodides; kinetic resolution; Sorogashira coupling;
D O I：
10.1016/j.tet.2008.04.057
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Na2S2O4-promoted radical addition reaction of perfluoroalkyl iodides with allenes has been studied in which a Z/E mixture of 2-iodo-1-perfluoroalkyl-2-alkenes 3 were afforded in 52-69% yields. A kinetic resolution using Sonogashira coupling reaction in MeCN using Et2NH as the base was developed to synthesize the 2-iodo-1-perfluoroalkyl-2(Z)-alkenes (Z-3) and E-4-perfluoroalkylmethylalk-4-en-2-ynois (E-5) stereoselectively. A complete Sonogashira coupling procedure in Et2NH at 40 degrees C was also developed affording a mixture of E and Z-4-perfluoroalkylmethyl-4-en-2-ynols (E-5 and Z-5), which may be easily separated by chromatography on silica gel. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6500 / 6509
页数：10
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