Description
Difluoromethyl 2-pyridyl sulfone, also known as Hu reagent, is a novel and efficient gem-difluoroolefination reagent for preparing gem-difluoroalkenes from both aldehydes and ketones. The fluorinated sulfinate intermediates during the gem-difluoroolefination is relatively stable, and can be halogenated in situ to afford bromo- and iododifluoromethyl compounds. It can also act as nucleophilic difluoro(sulfonato)methylation reagent for the synthesis of α,α-difluorosulfonates from aldehydes, and alkyl halides and triflates.
Uses
2-[(Difluoromethyl)sulfonyl]pyridine is a new novel gem-difluoroolefination reagent for both aldehydes and ketones.
Uses
Reagent is used in the olefination of ketones and aldehydes to form gem-difluoro olefins under basic conditions. Product is also used as a crucial intermediate toward making 1,1-difluorinated alkyl chains for the alkylation of heterocycles.
Reactions
(1) gem-Difluoroolefination of aldehydes and ketones.
(2) Halodifluoromethylation of aldehydes and ketones.
(3) (Fluorosulfonyl)difluoromethylation of aldehydes and ketones.
(4) Difluoro(sulfonato)methylation of alkyl halides and triflates.
(5) Aromatic difluoromethylation
General Description
Difluoromethyl 2-pyridyl sulfone (2-PySO
2CF
2H) is a reagent used in the
gem-difluoroolefination of aldehydes and ketones. It is also used as a reagent in the nucleophilic difluoro(sulfonato)methylation of alcohols,
N-sulfinyl imines, and halides.
References
[1] WENJUN MIAO. Nickel-Catalyzed Reductive 2-Pyridination of Aryl Iodides with Difluoromethyl 2-Pyridyl Sulfone[J]. Organic Letters, 2021, 23 3: 711-715. DOI:
10.1021/acs.orglett.0c03939.
[2] WENJUN MIAO. Nucleophilic Iododifluoromethylation of Carbonyl Compounds Using Difluoromethyl 2-Pyridyl Sulfone[J]. Organic Letters, 2016, 18 11: 2766-2769. DOI:
10.1021/acs.orglett.6b01258.[3] YANCHUAN ZHAO. Difluoromethyl 2-Pyridyl Sulfone: A New gem-Difluoroolefination Reagent for Aldehydes and Ketones[J]. Organic Letters, 2010, 12 7: 1444-1447. DOI:
10.1021/ol100090r.
