2924-74-5Relevant academic research and scientific papers
Electrophilic monofluoromethylation of O-, S-, and N-nucleophiles with chlorofluoromethane
Zhang, Wei,Zhu, Lingui,Hu, Jinbo
, p. 10569 - 10575 (2007)
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
Synthesis of Monofluoromethylthioesters from Aldehydes
Guo, Shi-Huan,Wang, Meng-Yue,Pan, Gao-Fei,Zhu, Xue-Qing,Gao, Ya-Ru,Wang, Yong-Qiang
, p. 1861 - 1869 (2018)
A direct and efficient approach to the synthesis of monofluoromethylthioesters from aldehydes has been developed. The synthetic method features mild reaction conditions, good tolerance of functional groups, a broad substrate scope, and especially no metal
(1S)-(?)-N-Monofluoromethylthio-7,7-dichloro-2,10-camphorsultam: An optically pure reagentfor asymmetric monofluoromethylthiolation
Zhang, He,Shen, Qilong
, (2021/10/29)
The development of an optically pure monofluoromethylthiolating reagent based on Oppolzer's camphorsultam auxiliary (1S)-(?)-N-monofluoromethylthio-7,7-dichloro-2,10-camphorsultam 1b was described. Reagents 1b reacted with two types of substrates including oxazolone and oxindole derivatives with good to excellent enantioselectivities under mild conditions, thus representing the first available method for us to access monofluoromethylthiolated stereogenic centers.
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.
Efficient Conversions of Thioethers to α-Fluoro Thioethers with DAST or DAST/Antimony(III) Chloride
Robins, Morris J.,Wnuk, Stanislaw F.
, p. 3800 - 3801 (2007/10/02)
Dialkyl or alkyl aryl thioethers, including nucleoside thioethers, undergo virtually quantitative conversion to α-fluoro thioethers with (diethylamino)sulfur trifluoride (DAST) in dichloromethane at ambient temperature.Antimony(III) chloride catalyzes the process.
α-Fluorination of Sulfides with N-Fluoropyridinium Triflates
Umemoto, Teruo,Tomizawa, Ginjiro
, p. 3625 - 3630 (2007/10/02)
The reaction of sulfides possessing α-hydrogen with various N-fuoropyridinium salts was examined.While the fluorinating power increased in the order of N-fluoro-2,4,6-trimethylpyridinium triflate 12, and 3 no longer produced the α-fluoro sulfide.Triflate 1 was more reactive than the corresponding tetrafluoroborate 4.Thus, it was shown that 1 satisfactorily fluorinated various kinds of sulfides under very mild conditions, giving α-fluoro sulfides.A two-step mechanism, oxidative fluorination of sulfur and Pummerer-type rearrangement, was proposed for the fluorination.The corresponding α-fluoro sulfoxide or sulfones were easily prepared from the sulfides by successive fluorination-oxidation procedure.
