Wu Fu-Peng, Lenz Madina, Suresh Adhya, Gogoi Achyut R, Tyler Jasper L, Daniliuc Constantin G, Gutierrez Osvaldo, Glorius Frank
Organisch-Chemisches Institut, Universität Münster Corrensstraße 40 48149 Münster Germany
Department of Chemistry, Texas A&M University 3255 TAMU, 580 Ross St 77843 College Station TX USA
Chem Sci. 2024 Aug 26;15(37):15205-11. doi: 10.1039/d4sc04413d.
The targeted and selective replacement of a single atom in an aromatic system represents a powerful strategy for the rapid interconversion of molecular scaffolds. Herein, we report a pyridine-to-benzene transformation nitrogen-to-carbon skeletal editing. This approach proceeds a sequence of pyridine ring-opening, imine hydrolysis, olefination, electrocyclization, and aromatization to achieve the desired transmutation. The most notable features of this transformation are the ability to directly install a wide variety of versatile functional groups in the benzene scaffolding, including ester, ketone, amide, nitrile, and phosphate ester fragments, as well as the inclusion of -substituted pyridines which have thus far been elusive for related strategies.
在芳香体系中对单个原子进行有针对性的选择性取代，是实现分子骨架快速相互转化的一种有效策略。在此，我们报道了一种吡啶到苯的转化——氮到碳的骨架编辑。该方法通过吡啶环开环、亚胺水解、烯化、电环化和芳构化一系列反应来实现所需的转变。这种转化最显著的特点是能够在苯骨架中直接引入多种通用官能团，包括酯基、酮基、酰胺基、腈基和磷酸酯片段，以及包含α-取代吡啶，而这是目前相关策略难以实现的。
