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(杂)芳基溴化物的脱羧镍和光氧化还原催化氨基羰基化反应

Decarboxylative Nickel- and Photoredox-Catalyzed Aminocarbonylation of (Hetero)Aryl Bromides.

作者信息

Hutskalova Valeriia, Bou Hamdan Farhan, Sparr Christof

机构信息

Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.

Syngenta Crop Protection AG, Crop Protection Research, Schaffhauserstrasse 101, CH-4332 Stein, Switzerland.

出版信息

Org Lett. 2024 Apr 12;26(14):2768-2772. doi: 10.1021/acs.orglett.3c02389. Epub 2023 Oct 5.

Abstract

An efficient methodology for the photoredox- and nickel-catalyzed aminocarbonylation of (hetero)aryl bromides was developed. The utilization of readily available oxamic acids, the application of a broadly used organic photoredox catalyst (4CzIPN), and mild reaction conditions make this transformation an appealing alternative to classical amidation procedures. The generation of carbamoyl radicals was supported by trapping reactions with a hydrogen atom transfer catalyst in the presence of DO, yielding the deuterated formamide. The generality of this deuteration protocol was confirmed for various oxamic acids.

摘要

开发了一种用于光氧化还原和镍催化的(杂)芳基溴化物氨基羰基化反应的高效方法。使用容易获得的草氨酸、应用广泛使用的有机光氧化还原催化剂(4CzIPN)以及温和的反应条件,使得这种转化成为经典酰胺化方法的一种有吸引力的替代方法。在DO存在下,通过与氢原子转移催化剂的捕获反应支持了氨基甲酰基自由基的生成,得到了氘代甲酰胺。各种草氨酸的这种氘代方案的通用性得到了证实。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19a8/11020166/29c72dc1e1d6/ol3c02389_0001.jpg

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