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铜催化有机硼酸频哪醇酯与一氧化碳的羧基化反应

Cu-catalyzed carboxylation of organoboronic acid pinacol esters with CO.

作者信息

Maeda Chihiro, Cho Takumi, Kumemoto Ren, Ema Tadashi

机构信息

Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan.

出版信息

Org Biomol Chem. 2023 Aug 16;21(32):6565-6571. doi: 10.1039/d3ob00938f.

Abstract

Chemical fixation of CO has received much attention. In particular, catalytic C-C bond formation with CO giving carboxylic acids is of great significance. Among the CO fixation methods, multiple carboxylation is one of the challenging subjects. Here we investigated the Cu-catalyzed carboxylation of a variety of boronic acid pinacol esters (C(sp)-, C(sp)-, and C(sp)-B compounds) with CO, which efficiently provided the corresponding products, including aryl, alkenyl, alkyl, and alkynyl carboxylic acids. This carboxylation was also applicable to multiple CO fixation giving di- and tri-carboxylic acids under robust reaction conditions (totally 29 examples).

摘要

一氧化碳的化学固定受到了广泛关注。特别是,通过一氧化碳进行催化碳-碳键形成以生成羧酸具有重要意义。在一氧化碳固定方法中,多重羧化是具有挑战性的课题之一。在此,我们研究了铜催化的多种硼酸频哪醇酯(C(sp²)-、C(sp³)-和C(sp)-B化合物)与一氧化碳的羧化反应,该反应能高效地提供相应产物,包括芳基、烯基、烷基和炔基羧酸。这种羧化反应在稳健的反应条件下也适用于多重一氧化碳固定以生成二羧酸和三羧酸(总共29个实例)。

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