Mono- and Difluoromethylation of 3(2 H)-Pyridazinones

Ziyue Zhu; Jiaqi Tang; Samantha Kyriazakos; Alexander Knieb; Yijie Xu; Chao Zhang; G K Surya Prakash

doi:10.1021/acs.orglett.4c03002

Mono- and Difluoromethylation of 3(2 H)-Pyridazinones

Org Lett. 2024 Sep 12. doi: 10.1021/acs.orglett.4c03002. Online ahead of print.

Authors

Ziyue Zhu¹, Jiaqi Tang¹, Samantha Kyriazakos¹, Alexander Knieb¹, Yijie Xu¹, Chao Zhang¹, G K Surya Prakash¹

Affiliation

¹ Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, United States.

PMID: 39264299
DOI: 10.1021/acs.orglett.4c03002

Abstract

A method for direct N-monofluoromethylation of pyridazinones with S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium triflate is disclosed. A method for the N- and O-difluoromethylated pyridazinones with TMSCF₂Br as the only promising difluorocarbene precursor is also reported. Substrates with various relevant functional groups, including analogues of Lynparza, are tolerated under both methods.