Reactivity of TEMPO anion as a nucleophile and its applications for selective transformations of haloalkanes or acyl halides to aldehydes
Reactivity of TEMPO anion as a nucleophile and its applications for selective transformations of haloalkanes or acyl halides to aldehydes
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DOI：
10.1016/j.tet.2004.09.067
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发表时间：
2004-12-13
期刊：
影响因子：
2.1
通讯作者：
Kawafuchi, H
中科院分区：
文献类型：
--
作者：
Inokuchi, T;Kawafuchi, H
2,2,6,6-四甲基哌啶-N-氧化物钠 (TEMPO-Na+)，由 TEMPO 还原生成。在THF中与萘钠反应，与烷基卤或酰基卤反应生成O-烷基化或酰化TEMPO，然后用mCPBA氧化或用DIBAL-H还原得到相应的醛，从而完成卤化物-羰基转化的新方案。 (C) 2004 Elsevier Ltd. 保留所有权利。
Sodium 2,2,6,6-tetramethylpiperidine-N-oxide (TEMPO-Na+), generated by reduction of TEMPO. with sodium naphthalenide in THF, reacted with alkyl halides or acyl halides to produce O-alkylated or acylated TEMPOs, which were in turn oxidized with mCPBA or reduced with DIBAL-H to afford the corresponding aldehydes, thus accomplishing a new protocol for the halides-carbonyls conversion. (C) 2004 Elsevier Ltd. All rights reserved.