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涉及硼-硼 σ 键“还原加成”到 4,4'-联吡啶的有机催化二硼化反应。

Organocatalytic diboration involving "reductive addition" of a boron-boron σ-bond to 4,4'-bipyridine.

机构信息

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University , Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

出版信息

J Am Chem Soc. 2015 Mar 4;137(8):2852-5. doi: 10.1021/jacs.5b00546. Epub 2015 Feb 19.

DOI:10.1021/jacs.5b00546
PMID:25669237
Abstract

A 4,4'-bipyridine-based catalyst system for diboration of pyrazine derivatives was established. The catalyst cycle consists of the following two steps: (1) reductive addition of the boron-boron bond of bis(pinacolato)diboron to 4,4'-bipyridine to form N,N'-diboryl-4,4'-bipyridinylidene and (2) oxidative boryl transfer from the intermediate to pyrazine to give N,N'-diboryl-1,4-dihydropyrazine with regeneration of 4,4'-bipyridine.

摘要

建立了一种用于吡嗪衍生物的双硼化反应的 4,4'-联吡啶基催化剂体系。催化剂循环包括以下两个步骤:(1)双(频哪醇)二硼的硼-硼键还原加成到 4,4'-联吡啶上,形成 N,N'-二硼基-4,4'-联吡啶亚基;(2)从中间体到吡嗪的氧化硼基转移,得到 N,N'-二硼基-1,4-二氢吡嗪,同时再生 4,4'-联吡啶。

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