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无过渡金属参与的从有机硼化合物构建 C-S、C-Se 和 C-Te 键。

Transition-Metal-Free C-S, C-Se, and C-Te Bond Formation from Organoboron Compounds.

机构信息

Laboratório de Síntese Orgânica Limpa - LASOL, CCQFA, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil.

出版信息

Chem Rec. 2021 Oct;21(10):2855-2879. doi: 10.1002/tcr.202100021. Epub 2021 Mar 18.

DOI:10.1002/tcr.202100021
PMID:33735500
Abstract

The present review describes the successful application of organoboron compounds in transition-metal-free C-S, C-Se, and C-Te bond formations. We presented studies regarding these C-Chalcogen bond formations using organoboron reagents, such as boronic acids, boronic esters, borate anions, and several sources of chalcogen atoms/moieties. Moreover, a broad range of transition-metal-free approaches to synthesize sulfides, selenides, and tellurides were described using conventional heating methods, which are sometimes green since they use green solvents, safe reagents, among others. Furthermore, protocols using alternative energy sources, including ultrasound, microwave irradiation, photocatalysis, and electrolytic processes, were also shown to be suitable. These protocols were applied to prepare a broad scope of functionalized chalcogenides with high molecular diversity. These studies and their proposed mechanisms were also reported herein in addition to the reuse of reaction promoters.

摘要

本文综述了有机硼化合物在过渡金属催化的 C-S、C-Se 和 C-Te 键形成反应中的成功应用。我们介绍了使用有机硼试剂(如硼酸、硼酸酯、硼酸根阴离子以及各种来源的硫原子/基团)进行这些 C-杂原子键形成的研究。此外,还描述了使用常规加热方法合成硫化物、硒化物和碲化物的广泛的无过渡金属方法,这些方法有时是绿色的,因为它们使用绿色溶剂、安全试剂等。此外,还展示了使用替代能源(包括超声波、微波辐射、光催化和电解过程)的方法也是适用的。这些方法被应用于制备具有高分子多样性的广泛范围的功能化的杂化物。本文还报道了这些研究及其提出的机制,以及反应促进剂的重复使用。

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