PHASE TRANSFER CATALYSIS - PREPARATION OF ALIPHATIC AND AROMATIC SULFONYL FLUORIDES
PHASE TRANSFER CATALYSIS - PREPARATION OF ALIPHATIC AND AROMATIC SULFONYL FLUORIDES
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DOI：
10.1021/jo00431a054
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发表时间：
1977-01-01
影响因子：
3.6
通讯作者：
CATE, LA
中科院分区：
文献类型：
--
作者：
BIANCHI, TA;CATE, LA
代理人（72-79%）。[11]然而，该试剂必须由仲胺、三甲基甲硅烷基氯和四氟化硫通过两个低收率步骤制备。12.近年来，涉及冠醚的固-液相转移催化作为有机合成的一种工具得到了广泛的应用。[13]在非质子溶剂中冠醚对阴离子的亲核增强作用是众所周知的。使用18-冠-6醚14催化与各种底物的氟/卤素交换也有文献记载; 15然而，据作者所知，文献中没有提到冠醚催化的与有机磺酰氯的氟化物交换反应。该反应通过在18-冠-6醚催化剂存在下，在乙腈溶液中或纯乙腈溶液中，在室温下搅拌磺酰氯和过量氟化钾来进行。通过该方法以非常高的产率制备了代表性的磺酰氟（参见表I）。
agent (72-79%). 11 The reagent, however, must be prepared in two low-yield steps from a secondary amine, trimethylsilyl chloride, and sulfur tetrafluoride. 12 In recent years, solid-liquid phase-transfer catalysis involving crown ethers has gained widespread use as a tool in organic synthesis. 13 The nucleophilic enhancement of anions by crown ethers in aprotic solvents is well known. The use of 18-crown-6 ether14 to catalyze fluorine/halogen exchange with a wide variety of substrates has also been documented; 15 however, to the best of the authors’ knowledge, no mention has been made in the literature of a crown ether catalyzed fluoride exchange reaction with organic sulfonyl chlorides. The reaction is conducted by stirring the sulfonyl chloride and excess potassium fluoride at room temperature in aceto-nitrile solution or neat in the presence of 18-crown-6 ether catalyst. Representative sulfonyl fluorides have been prepared by this method in very high yield (see Table I).18-crown-6 ether