REGIOSPECIFIC SYNTHESIS OF ARYL(2-FURYL)IODONIUM TOSYLATES, A NEW CLASS OF IODONIUM SALTS, FROM [HYDROXY(TOSYLOXY)IODO]ARENES AND 2-(TRIMETHYLSILYL)FURANS IN ORGANIC-SOLVENTS
REGIOSPECIFIC SYNTHESIS OF ARYL(2-FURYL)IODONIUM TOSYLATES, A NEW CLASS OF IODONIUM SALTS, FROM [HYDROXY(TOSYLOXY)IODO]ARENES AND 2-(TRIMETHYLSILYL)FURANS IN ORGANIC-SOLVENTS
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DOI：
10.1021/jo00163a022
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发表时间：
1983-01-01
影响因子：
3.6
通讯作者：
KOSER, GF
中科院分区：
文献类型：
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作者：
CARMAN, CS;KOSER, GF
在乙腈/甲醇中，2，5-双（三甲基硅基）呋喃与各种[羟基（对甲苯磺酰氧基）碘]芳烃（Arl（OH）OTs）反应，得到芳基[5-（三甲基硅基）-2-呋喃基]碘鎓对甲苯磺酸酯，产率为62%~ 80%。以2-甲基-5-（三甲基甲硅烷基）呋喃为底物，同样以61%至74%的产率获得芳基（5-甲基-2-呋喃基）碘鎓甲苯磺酸酯。[羟基（甲苯磺酰氧基）碘]芳烃与2-（三甲基甲硅烷基）呋喃在甲醇中反应，以低得多的产率（9-23%）得到芳基（2-呋喃基）碘鎓甲苯磺酸盐，并伴有高价有机碘组分的还原分解。据我们所知，这些是首次报道的芳基（呋喃基）碘鎓盐的例子。
The treatment of 2, 5-bis (trimethylsilyl) furan with various [hydroxy (tosyloxy) iodo] arenes (Arl (OH) OTs) in acetonitrile/methanol has been found to give aryl [5-(trimethylsilyl)-2-furyl] iodonium tosylates in yields ranging from 62% to 80%. With 2-methyl-5-(trimethylsilyl) furan as the substrate, aryl (5-methyl-2-furyl) iodonium tosylates are likewise obtained in yields ranging from 61% to 74%. The reactions of [hydroxy (tosyloxy) iodo] arenes with 2-(trimethylsilyl) furan in methanolgive aryl (2-furyl) iodonium tosylates in much lower yield (9—23%) and are accompanied by the reductive decomposition of the hypervalent organoiodine component. To our knowledge, these are the first reported examples of aryl (furyl) iodonium salts.