158607-43-3Relevant articles and documents
Monofluoromethyl-Substituted Sulfonium Ylides: Preparation, Structure-Reactivity Study and Substrate Scope?
Hong, Xin,Liu, Yafei,Lu, Long,Shen, Qilong
, p. 1317 - 1331 (2020)
Structure-reactivity study of a family of electrophilic monofluoromethylating reagents based on sulfonium ylide skeleton with different steric hindrance and electron-withdrawing properties was described. These studies led us to discover two highly reactive reagents 3 with a cyclic malonate backbone and 6 with an electron-poor 1,1,1,5,5,5-hexafluoropentane-2,4-dione backbone. The high reactivity of reagent 6 allowed to highly selectively access either C-monofluoromethylated or O-monofluoromethylated β-ketoesters in high yields by the use of different bases. In addition, reactions of reagent 3 with a variety of nucleophiles including phenols, carboxylic acids, thiophenols or heteroaryl nucleophiles occurred in full conversion within 10 min at room temperature and the scopes for these reactions were reported in detail.
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.
Electrophilic monofluoromethylation of O-, S-, and N-nucleophiles with chlorofluoromethane
Zhang, Wei,Zhu, Lingui,Hu, Jinbo
, p. 10569 - 10575 (2008/02/12)
CH2ClF has been found to be a useful electrophilic monofluoromethylating agent for a variety of O-, S-, and N-nucleophiles. The reaction is not sensitive to the radical scavenger such as nitrobenzene, which strongly supports an SN2 m
The Chemistry of Some 1-(α-Fluoroalkyl)Benzotriazoles
Katritzky, A.R.,Szajda, M.,Lam, J.N.
, p. 1243 - 1250 (2007/10/02)
1-(α-Fluoroalkyl)benzotriazoles are formed in high yields by treatment of their chloro precursors with potassium fluoride in 18-crown-6.The fluorine atom can then be displaced by methoxyarenes in the presence of a Lewis acid to afford 4-(α-substitutedalkyl)methoxyarenes. Key words: fluorination, methoxyarenes, aromatic substitution, benzyl ethers
