159831-89-7Relevant articles and documents
Electrolytic Partial Fluorination of Organic Compounds. 13. Selective Anodic α-Fluorination of Nitrogen-Containing Heterocyclic Sulfides and Its Application to the Synthesis of Fluorinated Fused Heterocycles
Erian, Ayman W.,Konno, Akinori,Fuchigami, Toshio
, p. 7245 - 7248 (1994)
Highly regioselective anodic monofluorination of 2-pyridyl 6-pyrimidinyl sulfides was successfully carried out and fluorinated fused heterocycles were readily prepared in good yields using an anodically fluorinated sulfide.
Direct monofluoromethylation of O-, S-, N-, and P-nucleophiles with PhSO(NTs)CH2F: The accelerating effect of α-fluorine substitution
Shen, Xiao,Zhou, Min,Ni, Chuanfa,Zhang, Wei,Hu, Jinbo
, p. 117 - 122 (2014/01/06)
An efficient and direct monofluoromethylation of O-, S-, N-, and P-nucleophiles with PhSO(NTs)CH2F 1 has been developed. In contrast to the previously known detrimental effect of α-fluorine substitution on SN2 reactions, the current monofluoromethylation is accelerated by the α-fluorine substitution. Based on a mechanistic study, a new reactivity of sulfoximine (as a radical monofluoromethylation reagent) is disclosed.
From olefination to alkylation: In-situ halogenation of julia-kocienski intermediates leading to formal nucleophilic iodo- and bromodifluoromethylation of carbonyl compounds
Zhao, Yanchuan,Gao, Bing,Hu, Jinbo
supporting information; experimental part, p. 5790 - 5793 (2012/05/07)
Iodo- and bromodifluoromethylated compounds are important synthetic intermediates and halogen-bond acceptors. However, direct introduction of -CF2I and -CF2Br groups through nucleophilic addition is particularly challenging because o
Electrolytic partial fluorination of organic compounds. 35. Anodic fluorination of 2-pyrimidyl, 2-pyridyl, and 2-quinazolinonyl sulfides
Dawood, Kamal M.,Higashiya, Seiichiro,Hou, Yankun,Fuchigami, Toshio
, p. 7935 - 7939 (2007/10/03)
Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron-withdrawing group (EWG) at the position α to the sulfur atom was successfully carried out using Et4NF·nHF (n = 3, 4) or Et3N·3HF as a supporting electrolyte and a fluoride ion source in 1,2- dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2- (fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with α,α-difluorinated product. In contrast, the corresponding 2- quinazolinonyl sulfides underwent similarly α-fluorination along with unexpected ipso-fluorination through anodic desulfurization.
Electrolytic Partial Fluorination of Organic Compounds. 19. A Novel Synthesis of Fluorothienopyridines Using Anodic Fluorination of Heterocyclic Sulfides as a Key Step
Erian, Ayman W.,Konno, Akinori,Fuchigami, Toshio
, p. 7654 - 7659 (2007/10/03)
Highly regioselective anodic monofluorination of 2-pyridyl and 4-pyrimidinyl sulfides bearing various electron-withdrawing groups were successfully carried out.The fluorinated sulfides were easily converted into 2-fluorothienopyridines in good yields.