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

页码：6500 / 6509

页数：10