A user-friendly entry to 2-iodoxybenzoic acid (IBX)
A user-friendly entry to 2-iodoxybenzoic acid (IBX)
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DOI：
10.1021/jo9824596
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发表时间：
1999-06-11
影响因子：
3.6
通讯作者：
Sputore, S
中科院分区：
文献类型：
--
作者：
Frigerio, M;Santagostino, M;Sputore, S
IBX，1-羟基-1，2-苯并氧基-3(1H)-酮-1-氧化物(2-碘氧基苯甲酸1)，虽然它在有机合成领域的存在仍然有限，主要是因为它在大多数有机溶剂中显著不溶。1，2b，3a 1983年，Dess和Martin报道，IBX可以通过在乙酸酐-醋酸混合物中加热1而转变为更易溶的环烷2，1，1，1-三乙酰氧基-1，1-二氢-1，2-苯并碘-3(1H)-酮。2从那时起，Dess-Martin Periphinane在醇顺利和选择性地转化为羰基化合物方面取得了显著的成功。2B除了用作Dess-Martin周期烷前驱体外，IBX本身在溶解于DMSO或悬浮于其他溶剂中时，还可用作功能化醇类的有价值的氧化剂。3试剂的一些应用强调了它作为一种温和的氧化剂的一般性4以及它进行精细转化的能力。特别是，IBX在不切割乙二醇CC键3a、5的情况下氧化Vic-diol，并允许
IBX, 1-hydroxy-1, 2-benziodoxol-3 (1H)-one 1-oxide (2-iodoxybenzoic acid 1), has been known for more than a century, although its presence on the scene of organic synthesis has remained limited primarily due to its remarkable insolubility in most organic solvents. 1, 2b, 3aIn 1983, Dess and Martin reported that IBX could be transformed into the far more soluble periodinane 2, 1, 1, 1-triacetoxy-1, 1-dihydro-1, 2-benziodoxol-3 (1H)-one, by warming 1 in an acetic anhydride-acetic acid mixture. 2 Since then, the Dess-Martin periodinane has met with remarkable success for the smooth and selective transformation of alcohols into carbonyl compounds. 2b Besides its use as the Dess-Martin periodinane precursor, IBX itself functions as a valuable oxidant of functionalized alcohols when dissolved in DMSO or suspended in other solvents. 3 A number of applications of the reagent have emphasized its generality as a mild oxidizing agent4 as well as its ability to perform delicate transformations. In particular, IBX oxidizes vic-diols without cleaving the glycol CC bond3a, 5 and allows the