Efficient Hydroxymethylation Reactions of Iodoarenes Using CO and 1,3-Dimethylimidazol-2-ylidene Borane

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• 作者：Takuji Kawamoto ; Takuma Okada ; Dennis P. Curran ; Ilhyong Ryu
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：May 3, 2013
• 年：2013
• 卷：15
• 期：9
• 页码：2144-2147
• 全文大小：240K
• 年卷期：v.15,no.9(May 3, 2013)
• ISSN：1523-7052

文摘

A hydroxymethylation reaction of a variety of iodoarenes proceeded effectively in the presence of CO, NHC-borane, diMeImd-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.