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A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C–H Alkylation of Alcohols
Synthesis ( IF 2.6 ) Pub Date : 2020-05-12 , DOI: 10.1055/s-0040-1707114
Kounosuke Oisaki 1 , Motomu Kanai 1 , Kentaro Sakai
Affiliation  

The development of catalyst-controlled, site-selective C(sp3)–H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid–ethanolamine complex enhances the chemical yield of the α-C–H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched­ peptides.

中文翻译:

弱键合硼酸盐催化剂,可改善醇的光氧化还原α-C-H烷基化作用的范围

催化剂控制的,位点选择性的C(sp 3)–H官能化反应的发展目前是有机合成中的主要挑战。在本文中,描述了一种新型的键弱化催化剂,该催化剂通过形成硼酸盐来识别醇的羟基。与可见光照射下的光氧化还原催化剂和氢原子转移催化剂结合使用时,缺电子的硼酸-乙醇胺络合物可提高醇类α-CH烷基化的化学收率。该三元杂化催化剂体系可以例如应用于富含官能团的肽。
更新日期:2020-05-12
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