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以碘作为终端氧化剂实现(杂)芳族羧酸的脱羧铃木-宫浦偶联反应。

Decarboxylative Suzuki-Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant.

作者信息

Quibell Jacob M, Duan Guojian, Perry Gregory J P, Larrosa Igor

机构信息

School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK.

出版信息

Chem Commun (Camb). 2019 May 30;55(45):6445-6448. doi: 10.1039/c9cc01817d.

DOI:10.1039/c9cc01817d
PMID:31099348
Abstract

A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling has been established. This process uses iodine or a bromine source as both the decarboxylation mediator and the terminal oxidant, thus avoiding the need for stoichiometric amounts of transition metal salts previously required. Our new protocol allows for the construction of valuable biaryl architectures through the coupling of (hetero)aromatic carboxylic acids with arylboronic acids. The scope of this decarboxylative Suzuki reaction has been greatly diversified, allowing for previously inaccessible non-ortho-substituted aromatic acids to undergo this transformation. The procedure also benefits from low catalyst loadings and the absence of stoichiometric transition metal additives.

摘要

一种用于脱羧铃木-宫浦型偶联的新方法已经建立。该过程使用碘或溴源作为脱羧介质和终端氧化剂,从而避免了以前所需的化学计量的过渡金属盐。我们的新方案允许通过(杂)芳族羧酸与芳基硼酸的偶联来构建有价值的联芳基结构。这种脱羧铃木反应的范围已经大大多样化,使得以前无法获得的非邻位取代的芳族酸能够进行这种转化。该方法还受益于低催化剂负载量和不存在化学计量的过渡金属添加剂。

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