Costantini Matteo, Mendoza Abraham
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
ACS Catal. 2021 Nov 5;11(21):13312-13319. doi: 10.1021/acscatal.1c03949. Epub 2021 Oct 18.
Chiral -cyclopropanes are strained rigid analogues of alkyl chains, whose study and application are limited by their difficult synthesis. A modular approach from olefin materials is enabled by the discovery of the electron donor-acceptor (EDA) interaction between 2-substituted benzothiazolines and -hydroxyphthalimide esters. These complexes are activated by visible light without photocatalysts, and the benzothiazoline reagent plays a triple role as a photoreductant, a stereoselective hydrogen-atom donor, and a Brønsted acid. Beyond the enantioselective synthesis of -cyclopropanes, these results introduce benzothiazolines as accessible and easily tunable self-sensitized photoreductants.
手性环丙烷是烷基链的张力刚性类似物，其研究和应用因合成困难而受到限制。2-取代苯并噻唑啉与羟基邻苯二甲酸酯之间电子给体-受体（EDA）相互作用的发现，实现了从烯烃材料出发的模块化方法。这些配合物在无光催化剂的情况下可被可见光活化，且苯并噻唑啉试剂兼具光还原剂、立体选择性氢原子供体和布朗斯特酸三重作用。除了对映选择性合成环丙烷外，这些结果还将苯并噻唑啉引入为可获取且易于调节的自敏化光还原剂。
