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通过与一氧化氮进行催化1,4-镍迁移实现C(sp)-H羟基化

C(sp)-H Hydroxylation via Catalytic 1,4-Ni Migration with NO.

作者信息

Zhang Huihui, Rodrigalvarez Jesus, Martin Ruben

机构信息

Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain.

Universitat Rovira i Virgili, Departament de Química Orgànica, c/Marcel·lí Domingo, 1, 43007 Tarragona, Spain.

出版信息

J Am Chem Soc. 2023 Aug 16;145(32):17564-17569. doi: 10.1021/jacs.3c07018. Epub 2023 Aug 2.

DOI:10.1021/jacs.3c07018
PMID:37531410
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10586377/
Abstract

Herein, we report a Ni-catalyzed C(sp)-H hydroxylation of aryl bromides with NO as an oxygen-atom donor. The reaction is enabled by a 1,4-Ni translocation that results in difunctionalized products. Regioselectivity and stereocontrol are dictated by a judicious choice of the ligand backbone, thus giving access to either carbonyl or phenol derivatives and offering an opportunity to repurpose hazardous substances en route to valuable oxygen-containing building blocks.

摘要

在此，我们报道了一种以一氧化氮作为氧原子供体的镍催化芳基溴的C(sp)-H羟基化反应。该反应通过1,4-镍迁移实现，生成双官能化产物。区域选择性和立体控制由配体骨架的明智选择决定，从而可得到羰基或苯酚衍生物，并为在合成有价值的含氧化合物中间体的过程中重新利用有害物质提供了机会。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d81/10586377/9eb62324094d/ja3c07018_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d81/10586377/49a23e69b9fc/ja3c07018_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d81/10586377/376bf1343e2c/ja3c07018_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d81/10586377/9eb62324094d/ja3c07018_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d81/10586377/49a23e69b9fc/ja3c07018_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d81/10586377/376bf1343e2c/ja3c07018_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d81/10586377/9eb62324094d/ja3c07018_0003.jpg

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镍催化的 NO 向 sp 杂化碳的氧转移。
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