3481-09-2Relevant articles and documents
A Two-Step, One-Pot, and Multigram-Scale Synthesis of N-Difluoromethylthiophthalimide
Zhu, Dianhu,Hong, Xin,Li, Dezhi,Lu, Long,Shen, Qilong
, p. 1383 - 1387 (2017)
A new method for the 100 g scale synthesis of N-difluoromethylthiophthalimide 1 from cheap commodity chemical benzyl mercaptan and HCF2Cl or other difluorocarbene precursors was described. Reagent 1 is an excellent electrophilic difluoromethylthiolating reagent as demonstrated by the gram-scale synthesis of five difluoromethylthiolated derivatives of structurally complicated drug-like molecules and natural products.
N-Chlorination-induced, oxidative ring contraction of 1,4-dimethoxyphthalazines
Im, Jeong Kyun,Yang, ByeongDo,Jeong, Ilju,Choi, Jun-Ho,Chung, Won-jin
supporting information, (2020/06/03)
A rarely explored oxidative ring contraction of electron-rich 1,2-diazine is described. Upon treatment with an electrophilic chlorinating reagent (TCICA), 1,4-dimethoxyphthalazines undergo an N-chlorination-induced ring contraction that is accompanied by the loss of one nitrogen atom. The scope of this unusual reactivity was examined with a range of 1,4-dimethoxyphthalazine derivatives. In addition, a mechanism proceeding via a bicyclic species was proposed on the basis of an isolated reaction intermediate and DFT calculations.
Organocatalytic Α-trifluoromethylthiolation of silylenol ethers: Batch vs continuous flow reactions
Abubakar, Said Said,Benaglia, Maurizio,Rossi, Sergio,Annunziata, Rita
, p. 94 - 101 (2017/09/25)
This work describes the organocatalytic α-trifluoromethylthiolation of silylenol ethers using N-(trifluoromethylthio)saccharin as trifluoromethylthiolating reagent that is activated by the presence of catalytic amounts of a Lewis base. Tetrahydrothiophene was identified as the best organocatalyst and it was successfully employed to promote the synthesis of different α-trifluoromethylketones; the reaction has been performed under a traditional batch methodology and under continuous flow conditions. In general, yields obtained using the traditional batch process were higher than those observed when the reaction was performed under flow conditions. However, short reaction times, higher productivity and higher space time yields were observed when a flow system process was employed. Preliminary DFT calculations were also performed in order to elucidate the mechanism of the reaction.