Ring-opening Difluorination of Pyrazoloazines
Ohki, H.; Komatsuda, M.; Kondo Jr., H.; Yamaguchi. J.
Tetrahedron. 2024, ASAP
DOI 10.1016/j.tet.2024.134020
Highlights In honour of Professor Thomas Maimone, 2024 Tetrahedron Young Investigator Award in Organic Synthesis

We have developed a novel ring-opening difluorination process for pyrazoloazines. Utilizing 2.5 equivalents of Selectfluor®, this method enables electrophilic difluorination and subsequent ring-opening of pyrazoloazines, yielding the corresponding difluoroalkylated azines. Additionally, our protocol extends to the decarbonylative difluorination of pyrazoloazines when starting with a formyl group at the C3 position, demonstrating the versatility and broad applicability of this approach. This advancement in difluorination chemistry offers a new pathway for the synthesis of difluorinated compounds, potentially enriching the toolkit for practitioners in medicinal chemistry and materials science.