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

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

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

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.

Original language	English (US)
Pages (from-to)	8106-8109
Number of pages	4
Journal	Organic Letters
Volume	26
Issue number	38
DOIs	https://doi.org/10.1021/acs.orglett.4c03002
State	Published - Sep 27 2024
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Mono- and Difluoromethylation of 3(2H)-Pyridazinones",

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.",

author = "Ziyue Zhu and Jiaqi Tang and Samantha Kyriazakos and Alexander Knieb and Yijie Xu and Chao Zhang and Prakash, {G. K.Surya}",

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T1 - Mono- and Difluoromethylation of 3(2H)-Pyridazinones

AU - Zhu, Ziyue

AU - Tang, Jiaqi

AU - Kyriazakos, Samantha

AU - Knieb, Alexander

AU - Xu, Yijie

AU - Zhang, Chao

AU - Prakash, G. K.Surya

PY - 2024/9/27

Y1 - 2024/9/27

N2 - 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.

AB - 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.

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SN - 1523-7060

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EP - 8109

JO - Organic Letters

JF - Organic Letters

IS - 38

ER -

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

Abstract

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