Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
J Am Chem Soc. 2020 Apr 22;142(16):7598-7605. doi: 10.1021/jacs.0c01724. Epub 2020 Apr 6.
A photoassisted Ni-catalyzed reductive cross-coupling between tosyl-protected alkyl aziridines and commercially available (hetero)aryl iodides is reported. This mild and modular method proceeds in the absence of stoichiometric heterogeneous reductants and uses an inexpensive organic photocatalyst to access medicinally valuable β-phenethylamine derivatives. Unprecedented reactivity was achieved with the activation of cyclic aziridines. Mechanistic studies suggest that the regioselectivity and reactivity observed under these conditions are a result of nucleophilic iodide ring opening of the aziridine to generate an iodoamine as the active electrophile. This strategy also enables cross-coupling with Boc-protected aziridines.
报道了一种光辅助的 Ni 催化的 tosyl 保护的烷基氮丙啶与市售（杂）芳基碘化物之间的还原交叉偶联。这种温和且模块化的方法在没有化学计量的非均相还原剂的情况下进行，并使用廉价的有机光催化剂来获得具有药用价值的 β-苯乙胺衍生物。通过环状氮丙啶的活化实现了前所未有的反应性。机理研究表明，在这些条件下观察到的区域选择性和反应性是氮丙啶的亲核碘环开环的结果，生成碘胺作为活性亲电试剂。该策略还可用于与 Boc 保护的氮丙啶进行交叉偶联。
