Efficient Hydroxymethylation Reactions of Iodoarenes Using CO and 1,3-Dimethylimidazol-2-ylidene Borane
Efficient Hydroxymethylation Reactions of Iodoarenes Using CO and 1,3-Dimethylimidazol-2-ylidene Borane
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DOI：
10.1021/ol4006294
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发表时间：
2013-05-03
期刊：
影响因子：
5.2
通讯作者：
Rye, Ilhyong
中科院分区：
文献类型：
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作者：
Kawamoto, Takuji;Okada, Takuma;Rye, Ilhyong
在CO， nhc -硼烷，diMelmd-BH3(2)作为自由基介质和AIBN的催化量存在下，多种碘芳烃的羟甲基化反应有效进行。反应发生在芳基碘键而不是芳基溴键和芳基氯键上。由芳基碘化物、一氧化碳和缺电子烯烃组成的三组分偶联反应也进行得很好，得到了产率很高的不对称酮。对照实验表明，2可作为酰基自由基的氢供体，碘化nhc -硼烷可作为醛的还原剂。
A hydroxymethylation reaction of a variety of iodoarenes proceeded effectively in the presence of CO, NHC-borane, diMelmd-BH3 (2) as a radical mediator, and a catalytic amount of AIBN. The reaction took place chemoselectively at the aryl-iodine bond but not at the aryl-bromine and aryl-chlorine bonds. A three-component coupling reaction comprising aryl iodides, CO, and electron-deficient alkenes also proceeded well to give unsymmetrical ketones in good yields. Control experiments show that 2 would act as a hydrogen donor to acyl radicals and iodinated NHC-borane as a reducing agent of aldehydes.