Centre for Synthesis and Chemical Biology, Department of Chemistry, Royal College of Surgeons in Ireland, Dublin 2, Ireland.
Org Lett. 2022 Jul 8;24(26):4729-4733. doi: 10.1021/acs.orglett.2c01494. Epub 2022 Jun 28.
The first example of an aromatic haloform reaction is reported, defining a conceptually new haloform-type approach to the metal-free functionalization of arenes. We demonstrated that heteroarenes bearing a vinylogous nitromethane system, via the stage of a trichloromethane derivative, could undergo aromatic amination to produce N-functionalized arenes in quantitative yields and without the need for transition-metal catalysis. The haloform-type amination was implemented in the development of effective orthogonal N-protection strategies, establishing a new promising N-protecting reagent.
首例芳香卤仿反应的例子被报道，为芳烃的无金属官能化定义了一种全新卤仿型方法。我们证明了带有亚硝酮系统的杂芳烃，通过三氯甲烷衍生物阶段，可以进行芳基胺化反应，以定量产率和无需过渡金属催化生成 N-官能化芳烃。卤仿型胺化反应被应用于有效正交 N-保护策略的开发，建立了一种新的有前途的 N-保护试剂。
