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双(碘锌基)甲烷和双(碘锌基)乙烷与两种不同有机卤化物的过渡金属催化顺序交叉偶联反应。

Transition-metal-catalyzed sequential cross-coupling of bis(iodozincio)methane and -ethane with two different organic halides.

作者信息

Yoshino Hideaki, Toda Narihiro, Kobata Masami, Ukai Katsumi, Oshima Koichiro, Utimoto Kiitiro, Matsubara Seijiro

机构信息

Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai-katsura, Nishikyo, Japan.

出版信息

Chemistry. 2006 Jan 11;12(3):721-6. doi: 10.1002/chem.200500767.

Abstract

Bis(iodozincio)methane, prepared from diiodomethane and zinc, reacts with an organic halide in the presence of a transition-metal catalyst to give an iodozinciomethylenated compound; this then reacts with another organic halide to form a C--C bond. The overall process connects two electrophiles with one carbon atom. Bis(iodozincio)ethane can also undergo this transformation, yielding a new stereogenic center. The asymmetric induction of this stereogenic center was investigated by using a chiral palladium catalyst.

摘要

由二碘甲烷和锌制备的双(碘锌基)甲烷,在过渡金属催化剂存在下与有机卤化物反应,生成碘锌基亚甲基化化合物;该化合物再与另一种有机卤化物反应形成碳 - 碳键。整个过程通过一个碳原子连接两个亲电试剂。双(碘锌基)乙烷也能发生这种转化,产生一个新的手性中心。使用手性钯催化剂研究了这个手性中心的不对称诱导作用。

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