Radical Carboxylation: Ester Synthesis from Alkyl Iodides, Carbon Monoxide, and Alcohols under Irradiation Conditions

Radical Carboxylation: Ester Synthesis from Alkyl Iodides, Carbon Monoxide, and Alcohols under Irradiation Conditions
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DOI:
10.1021/ja964124g
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发表时间:
1997-06
影响因子:
15
通讯作者:
K. Nagahara;I. Ryu;M. Komatsu;N. Sonoda
K. Nagahara;I. Ryu;M. Komatsu;N. Sonoda
中科院分区:
化学1区
文献类型:
--
作者:
K. Nagahara;I. Ryu;M. Komatsu;N. Sonoda

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毫无疑问,过渡金属催化的有机卤化物与CO的羰基化得到羧酸及其衍生物是一种基本和重要的合成方法(方程式1)。1,2众所周知,孟山都化学公司从甲醇和CO生产乙酸,该工艺的关键步骤涉及Rh催化的甲基碘羰基化生成乙酰碘。3然而,在本文中,我们报道了一种概念上的新方法,用于从烷基碘、醇和CO的组合合成羧酸酯,该方法可以在没有金属催化剂的情况下用光照射进行(等式2)。4在我们以前的论文中,我们报道了通过光解
There is little doubt that transition metal-catalyzed carbonylation of organic halides with CO to give carboxylic acids and their derivatives is a basic and important synthetic process (eq 1). 1, 2 It is well-known that the Monsanto Chemical Company produces acetic acid from methanol and CO and that a key step in this process involves the Rh-catalyzed carbonylation of methyl iodide to give acetyl iodide. 3 In this paper, however, we report a conceptually new method for the synthesis of carboxylic acid esters from the combination of alkyl iodides, alcohols, and CO that can be carried out with photoirradiation in the absence of a metal catalyst (eq 2). 4 In our previous paper, we reported the synthesis of acyl selenides by the photolysis of