1131-33-5Relevant articles and documents
2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds
Muta, Ryuhei,Torigoe, Takeru,Kuninobu, Yoichiro
, (2019)
The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.
Arylation of pyridine N-oxides via a ligand-free Suzuki reaction in water
Liu, Chun,Zhang, Shao-Ke,Zhang, Yi-Xia,Jin, Zi-Lin
, p. 55 - 57 (2015)
We report a practical and highly efficient protocol for the arylation of pyridine N-oxides with arylboronic acid through palladium-catalyzed Suzuki reaction in water. This ligand-free Suzuki reaction is performed in the presence of diisopropylamine and gi
2-Position-selective C[sbnd]H fluoromethylation of six-membered heteroaryl N-oxides with (fluoromethyl)triphenylphosphonium iodide
Hu, Chen-Chen,Hu, Wei-Qiang,Qing, Feng-Ling,Xu, Xiu-Hua
, (2021)
A mild and efficient method for the regioselective C[sbnd]H fluoromethylation of heteroaryl N-oxides with (fluoromethyl)triphenylphosphonium iodide is presented. With LiOt-Bu as the base and DMSO as the solvent, this reaction delivers a series of C2-fluor
A Photosensitizer-Free Radical Cascade for Synthesizing CF3-Containing Polycyclic Quinazolinones with Visible Light
Hu, Qiang,Yu, Wan-Lei,Luo, Yong-Chun,Hu, Xiu-Qin,Xu, Peng-Fei
supporting information, p. 1493 - 1501 (2022/02/07)
Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction of N-cyanamide alkenes for the synthesis of functionalized quinazolinones. Importantly, the reaction is carried out under mild conditions without any addi
Visible-Light-Induced ortho-Selective Migration on Pyridyl Ring: Trifluoromethylative Pyridylation of Unactivated Alkenes
Jeon, Jinwon,He, Yu-Tao,Shin, Sanghoon,Hong, Sungwoo
supporting information, p. 281 - 285 (2019/11/26)
The photocatalyzed ortho-selective migration on a pyridyl ring has been achieved for the site-selective trifluoromethylative pyridylation of unactivated alkenes. The overall process is initiated by the selective addition of a CF3 radical to the alkene to provide a nucleophilic alkyl radical intermediate, which enables an intramolecular endo addition exclusively to the ortho-position of the pyridinium salt. Both secondary and tertiary alkyl radicals are well-suited for addition to the C2-position of pyridinium salts to ultimately provide synthetically valuable C2-fluoroalkyl functionalized pyridines. Moreover, the method was successfully applied to the reaction with P-centered radicals. The utility of this transformation was further demonstrated by the late-stage functionalization of complex bioactive molecules.