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温和光介导铁催化下羧酸的脱羧磺酰化反应

Decarboxylative Sulfonylation of Carboxylic Acids under Mild Photomediated Iron Catalysis.

作者信息

Dong Yuanqi, Xiong Ni, Rong Zhouting, Zeng Rong

机构信息

School of Chemistry, Xi'an Jiaotong University, Xi'an 710049, P. R. China.

Hwamei College of Life and Health Sciences, Zhejiang Wanli University, Ningbo 315100, China.

出版信息

Org Lett. 2024 Mar 29;26(12):2381-2386. doi: 10.1021/acs.orglett.4c00410. Epub 2024 Mar 15.

Abstract

Organic sulfones are an important class of chemical compounds widely used in many research fields. The direct decarboxylative sulfonylation of carboxylic acids is attractive but challenging, particularly when iron is used as a metal catalyst. Herein, we describe a photoinduced iron-catalytic method for the synthesis of sulfones directly using carboxylic acids via a radical-based decarboxylation. This protocol is mild, highly efficient, and easy-to-operate. A broad scope of carboxylic acids and carbon electrophiles could be well tolerated. A mechanism involving the iron-catalyzed decarboxylation, radical transfer, single-electron reduction, and nucleophilic attack is proposed.

摘要

有机砜是一类重要的化合物,广泛应用于许多研究领域。羧酸的直接脱羧磺酰化反应很有吸引力,但具有挑战性,特别是当使用铁作为金属催化剂时。在此,我们描述了一种光诱导铁催化方法,通过基于自由基的脱羧反应直接使用羧酸合成砜。该方法温和、高效且易于操作。广泛的羧酸和碳亲电试剂都能被很好地耐受。提出了一种涉及铁催化脱羧、自由基转移、单电子还原和亲核攻击的机理。

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