16255-53-1Relevant academic research and scientific papers
Fluorium-Initiated Dealkylative Cyanation of Thioethers to Thiocyanates
Chen, Yang,Qi, Hongyi,Chen, Ning,Ren, Demin,Xu, Jiaxi,Yang, Zhanhui
, p. 9044 - 9050 (2019/08/12)
Thioethers are converted to thiocyanates via fluorium-initiated dealkylative cyanation. Selectfluor is used as the oxidant, and trimethylsilyl cyanide is used as the cyanation reagent. The well-streamlined procedure is user-friendly, operationally simple, and step-economical. The current mechanistic studies show that the sulfur radical cation and cyano radical are both involved. They combine to deliver cyanosulfonium, an intermediate toward thiocyanate after dealkylation. Alternatively, a nucleophilic mechanism is also possible. Our dealkyaltive cyanation is also efficient in synthesizing thiocyanates with strongly electrophilic functionalities.
N -Thiocyanato-dibenzenesulfonimide: A new electrophilic thiocyanating reagent with enhanced reactivity
Li, Chengqiu,Long, Pingliang,Wu, Haopeng,Yin, Hongquan,Chen, Fu-Xue
supporting information, p. 7131 - 7134 (2019/08/07)
A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding thicyanate derivatives in high yields, while TfOH for unactivated arenes and hetero aromatics and Zn(OTf)2 for ketones was used as the catalyst, respectively. It is noteworthy that internal alkenes and styrenes were bifunctionalized giving 1,2-amino thiocyanates in high yields.
Direct Photocatalytic S-H Bond Cyanation with Green cN Source
Guo, Wei,Tan, Wen,Zhao, Mingming,Zheng, Lvyin,Tao, Kailiang,Chen, Deliang,Fan, Xiaolin
supporting information, p. 6580 - 6588 (2018/05/29)
Herein we report a novel C-S bond cleavage and reconstruction strategy for the synthesis of thiocyanates through direct photocatalytic S-H bond cyanation from thiols and inorganic thiocyanate salts. In our strategy, the unprecedented example of cutting off C-S bond of SCN- to deliver the green CN sources is demonstrated. This transformation features nontoxic and inexpensive CN sources, available starting materials, metal-/base-/ligand-/peroxide-free, high step economy and mild conditions. It leads to the construction of various thiocyanates and some medicinally and biologically active thiocyanate-containing molecules.
Transition-metal-free synthesis of thiocyanato- or nitro-arenes through diaryliodonium salts
Li, Xiao-Hua,Li, Liang-Gui,Mo, Xue-Ling,Mo, Dong-Liang
, p. 963 - 970 (2016/07/07)
A transition-metal-free approach to facile synthesis of thiocyanato- and nitro-arenes was developed from KSCN (potassiumthiocyanate) or NaNO2with diaryliodonium salts in good yields under mild conditions. The reaction was compatible with a variety of sensitive functional substituents such as halides and nitro and ester groups. The usefulness of arylation products has been realized. (Formula Present).
General and practical formation of thiocyanates from thiols
Frei, Reto,Courant, Thibaut,Wodrich, Matthew D.,Waser, Jerome
supporting information, p. 2662 - 2668 (2015/02/05)
A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational studies indicated a low energy concerted transition state for the cyanation of the thiolate anion or radical. The developed thiocyanate synthesis has broad potential for various applications in synthetic chemistry, chemical biology and materials science.
