Conversion of (sp3)C-F bonds of alkyl fluorides to (sp3)C-heteroatom (heteroatom = I, SR, SeR, TeR) bonds by the use of magnesium reagents having heteroatom substituents

Conversion of (sp3)C-F bonds of alkyl fluorides to (sp3)C-heteroatom (heteroatom = I, SR, SeR, TeR) bonds by the use of magnesium reagents having heteroatom substituents
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DOI:
10.1246/cl.2007.196
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发表时间:
2007-01-05
期刊:
影响因子:
1.6
通讯作者:
Kambe, Nobuaki
Kambe, Nobuaki
中科院分区:
化学4区
文献类型:
--
作者:
Begum, Shameem Ara;Terao, Jun;Kambe, Nobuaki

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本文提出了一种将(sp(3))C-F键转化为(sp(3))C-Z(Z = I,SR,SeR,TeR)键的简便方法。反应在室温下使用镁盐(Z-MgX)进行。在醚溶液中,Mg I_2取代伯烷基氟的S(N)_2机理得到了与F相连的碳的立体化学反转的支持。
A convenient method for conversion of (sp(3))C-F bonds to (sp(3))C-Z (Z = I, SR, SeR, TeR) bonds has been developed. The reaction proceeds at room temperature using magnesium salts (Z-MgX). S(N)2 mechanism for substitiution of primary alkyl fluorides with MgI2 in ether was supported by the inversion of the stereochemistry of the carbon connecting to F.