Shoji Toshitaka, Fukushima Kosuke, Menjo Takayuki, Yamada Yoichi, Hanasaki Tomonori, Kikushima Kotaro, Takenaga Naoko, Dohi Toshifumi
College of Pharmaceutical Sciences, Ritsumeikan University.
Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University.
Chem Pharm Bull (Tokyo). 2021 Sep 1;69(9):886-891. doi: 10.1248/cpb.c21-00380. Epub 2021 Jun 18.
Functionalized nucleobases are utilized in a wide range of fields; therefore, the development of new synthesis methods is essential for their continued application. With respect to the C-arylation of halopurines, which possess a substituent at the N-position, only a small number of successful cases have been reported, which is predominately a result of large steric hinderance effects. Herein, we report efficient and metal-free C-arylations and SAr reactions of N-substituted chloropurines in aromatic and heteroatom nucleophiles promoted by triflimide (TfNH) in fluoroalcohol.
功能化核碱基被广泛应用于众多领域;因此,开发新的合成方法对其持续应用至关重要。关于在N位带有取代基的卤代嘌呤的C-芳基化反应,仅报道了少数成功案例,这主要是由于较大的空间位阻效应。在此,我们报道了在氟代醇中由三氟甲磺酰亚胺(TfNH)促进的N-取代氯嘌呤与芳香族和杂原子亲核试剂之间高效且无金属的C-芳基化反应和SAr反应。