温和条件下Pd/π-酸配体催化的芳基碘化物和烷基铟试剂的交叉偶联反应

doi:10.6023/A12030075

化学学报 ›› 2012, Vol. 70 ›› Issue (14): 1538-1542.DOI: 10.6023/A12030075 上一篇下一篇

研究论文

温和条件下Pd/π-酸配体催化的芳基碘化物和烷基铟试剂的交叉偶联反应

靳立群, 罗贤才, 雷爱文

武汉大学化学与分子科学学院武汉 430072

投稿日期:2012-03-30 发布日期:2012-05-03
通讯作者: 雷爱文
基金资助:
项目受国家自然科学基金(Nos. 21025206, 20832003和20972118)和教育部学术新人奖资助.

Pd/π-Acidic Ligand Catalyzed ArI and Alkyl-In Cross-CouplingReactions under Mild Conditions

Jin Liqun, Luo Xiancai, Lei Aiwen

College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072

Received:2012-03-30 Published:2012-05-03
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21025206, 20832003 and 20972118) and Academic Award for Excellent Ph.D. Candidates Funded by Ministry of Education of China.

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1. 温和条件下Pd/π-酸配体催化的芳基碘化物和烷基铟试剂的交叉偶联反应.PDF(653KB)

摘要/Abstract

过渡金属催化的偶联反应是构建C—C键的重要途径. 目前主要的催化剂为钯络合物, 且对于Csp²-Csp²报道的是最多的, 而Csp³相关成键的报道则相对少一些, 主要是因为其涉及的还原消除较慢. 我们曾发现π-酸类配体可以很好地促进Csp³-Pd-Csp²的还原消除, 这对于Csp³相关的成键具有重要意义. 报道了以膦烯烃、双烯化合物等π-酸化合物作为配体时, 在温和条件下高选择性地实现了钯催化的芳基碘化物和烷基铟试剂的交叉偶联反应, 构建Csp³-ArCsp²键. 其中伯碳和仲碳的烷基铟试剂均可以很好的兼容; 另外, 进一步的研究表明, 反应可以在敞口的条件下进行, 对水和氧气可以兼容, 并可以得到较高的产率.

关键词: 钯, π-酸配体, 芳基碘, 烷基铟试剂

Transition metal-catalyzed coupling reaction is an important approach to form C—C bond, in which palladium is the most popularly used catalyst. Up to now, the formation of Csp²-Csp² has been widely reported in the presence of palladium catalysts. However, Csp³-related bond formations are relatively less demonstrated owing to the slow reductive elimination of the corresponding Pd species. We have reported that π-acidic ligand could promote the reductive elimination of Csp³-Pd-Csp², which is significant to construct Csp³-C bond. In this comunication, with Pd/π-acidic ligand as the catalyst, ArI and alkylindium reagents could be coupled together under mild conditions in high selectivity to form Csp²-ArCsp³ bond. Primary and secondary alkylindium could be tolerated. Moreover, further studies indicated that the reaction could be performed well when the reactions were open to air, suggesting that the reaciton was insensitive towards moisture and oxygen.

Key words: palladium, π-acidicligand, ArI, alkylindium reagents

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靳立群, 罗贤才, 雷爱文. 温和条件下Pd/π-酸配体催化的芳基碘化物和烷基铟试剂的交叉偶联反应[J]. 化学学报, 2012, 70(14): 1538-1542.

Jin Liqun, Luo Xiancai, Lei Aiwen. Pd/π-Acidic Ligand Catalyzed ArI and Alkyl-In Cross-CouplingReactions under Mild Conditions[J]. Acta Chimica Sinica, 2012, 70(14): 1538-1542.

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温和条件下Pd/π-酸配体催化的芳基碘化物和烷基铟试剂的交叉偶联反应

Pd/π-Acidic Ligand Catalyzed ArI and Alkyl-In Cross-CouplingReactions under Mild Conditions

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