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有机分子的光介导硒官能化:最新进展。

Light-Mediated Seleno-Functionalization of Organic Molecules: Recent Advances.

机构信息

Instituto de Química (INQUI), Universidade Federal de Mato Grosso do Sul -UFMS, Campo Grande, 79074-460, MS -, Brazil.

Departamento de Química, Universidade Federal do Paraná (UFPR), Curitiba, 81531-990, PR Brazil.

出版信息

Chem Rec. 2021 Oct;21(10):2739-2761. doi: 10.1002/tcr.202100006. Epub 2021 Mar 3.

Abstract

Organoselenium compounds constitute an important class of substances with applications in the biological, medicinal and material sciences as well as in modern organic synthesis, attracting considerable attention from the scientific community. Therefore, the construction of the C-Se bond via facile, efficient and sustainable strategies to access complex scaffolds from simple substrates are an appealing and hot topic. Visible light can be regarded as an alternative source of energy and is associated with environmentally-friendly processes. Recently, the use of visible-light mediated seleno-functionalization has emerged as an ideal and powerful route to obtain high-value selenylated products, with diminished cost and waste. This approach, involving photo-excited substrates/catalyst and single-electron transfer (SET) between substrates in the presence of visible light has been successfully used in the versatile and direct insertion of organoselenium moieties in activated and unactivated C(sp )-H, C(sp )-H, C(sp)-H bonds as well as C-heteroatom bonds. In most cases, ease of operation and accessibility of the light source (LEDs or commercial CFL bulbs) makes this approach more attractive and sustainable than the traditional strategies.

摘要

有机硒化合物是一类重要的物质,在生物、医学和材料科学以及现代有机合成中都有应用,引起了科学界的极大关注。因此,通过简便、高效和可持续的策略构建 C-Se 键,从简单的底物中获得复杂的支架,是一个吸引人的热门话题。可见光可以被视为一种替代能源,并且与环保工艺相关。最近,可见光介导的硒官能化的应用已经成为获得高价值硒化产物的理想而强大的途径,降低了成本和浪费。这种方法涉及光激发底物/催化剂和可见光存在下底物之间的单电子转移 (SET),已经成功地用于在活化和未活化的 C(sp )-H、C(sp )-H、C(sp )-H 键以及 C-杂原子键中灵活和直接地插入有机硒基团。在大多数情况下,操作的简便性和光源(LED 或商业 CFL 灯泡)的可及性使得这种方法比传统策略更具吸引力和可持续性。

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