Characterization of the Nucleophilic Allylindium Species Generated from Allyl Bromide and Indium(0) in Aqueous Media
Characterization of the Nucleophilic Allylindium Species Generated from Allyl Bromide and Indium(0) in Aqueous Media
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DOI：
10.1002/ejoc.201000956
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发表时间：
2010-10
影响因子：
2.8
通讯作者：
M. Yasuda;Masa-aki Haga;Y. Nagaoka;A. Baba
中科院分区：
文献类型：
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作者：
M. Yasuda;Masa-aki Haga;Y. Nagaoka;A. Baba
烯丙基溴和铟（0）在水中的还原体系生成单烯丙基二溴化铟（III）和双烯丙基溴化铟（III）。这些化合物分别与3，5-二溴吡啶或4-（二甲氨基）吡啶络合后，通过X射线分析进行表征。两种配合物均表现出较高的亲核性，并与苯甲醛反应生成烯丙基化产物。二烯丙基溴化铟（III）在水中的稳定性低于单烯丙基二溴化铟（III）。二烯丙基铟（III）与二苯甲醇反应生成亲核性的（μ-烷氧基）铟物种。这一结果表明，烯丙基（μ-羟基）铟在水相Barbie型反应体系中也起亲核试剂的作用。
The reductive system of allyl bromide and indium(0) in water generated monoallylindium(III) dibromide and diallylindium(III) bromide. These compounds were characterized by X-ray analysis after complexation with 3,5-dibromopyridine or 4-(dimethylamino)pyridine, respectively. Both isolated complexes showed high nucleophilicity and reacted with benzaldehyde to give the allylation product. The diallylindium(III) bromide was less stable in water than the monoallylindium(III) dibromide. The reaction of the diallylindium(III) with benzhydrol gave a (μ-alkoxido)indium species that showed nucleophilicity. This result suggests that allyl(μ-hydroxido)indium also acted as a nucleophile in an aqueous Barbie-type reaction system.