Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective and neutral system for the facile conversion of alcohols, thiols and selenols to alkyl halides in the presence of halide ions
Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective and neutral system for the facile conversion of alcohols, thiols and selenols to alkyl halides in the presence of halide ions
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DOI：
10.1016/s0040-4020(02)01089-x
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发表时间：
2002-10-21
期刊：
影响因子：
2.1
通讯作者：
Vaezzadeh, AR
中科院分区：
文献类型：
--
作者：
Iranpoor, N;Firouzabadi, H;Vaezzadeh, AR
三苯基膦 (Ph3P) 和 2,3-二氯-5,6-二氰基苯醌在 CH2Cl2 中的混合物产生络合物，在 R4NX (X = Cl、Br、I) 存在下，该络合物在室温下以高产率将醇、硫醇和硒醇转化为其相应的烷基卤。该方法对于在 2 度醇存在下转化 1 度醇以及在 3 度醇、硫醇、环氧化物、三甲基甲硅烷基醚和四氢吡喃基醚、1,3 二噻烷、二硫化物和酰胺存在下转化 V 醇和 2 度醇具有高度选择性。 (C) 2002 Elsevier Science Ltd. 保留所有权利。
A mixture of triphenylphosphine (Ph3P) and 2,3-dichloro-5,6-dicyanobenzoquinone in CH2Cl2 affords a complex which in the presence of R4NX (X = Cl, Br, I) converts alcohols, thiols and selenols into their corresponding alkyl halides in high yields at room temperature. The method is highly selective for the conversion of 1degrees alcohols in the presence of 2degrees ones and also V and 2degrees alcohols in the presence of 3degrees alcohols, thiols, epoxides, trimethylsilyl- and tetrahydropyranyl ethers, 1,3 dithianes, disulfides, and amides. (C) 2002 Elsevier Science Ltd. All rights reserved.