1879-21-6Relevant articles and documents
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 cross-coupling of thioethers with aryl(cyano)iodonium triflates: A facile and efficient method for the one-pot synthesis of thiocyanates
Zhu, Dan,Chang, Denghu,Shi, Lei
supporting information, p. 7180 - 7183 (2015/04/27)
A novel transition-metal-free cross-coupling method for the one-step synthesis of thiocyanates via the C-S bond cleavage of readily available thioethers with aryl(cyano)-iodonium triflates as the cyanating agent is developed. This process features relatively broad substrate scopes, less-toxic hypervalent iodine reagents, mild operating conditions, excellent functional group compatibilities, and affords various thiocyanates in moderate to good yields. This journal is
DNA Alkylation by leinamycin can be triggered by cyanide and phosphines
Zang, Hong,Breydo, Leonid,Mitra, Kaushik,Dannaldson, Jeffrey,Gates, Kent S.
, p. 1511 - 1515 (2007/10/03)
Previous work has shown that alkylation of DNA by the antitumor agent leinamycin (1) is potentiated by reaction of the antibiotic with thiols. Here, it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin. Overall, the results suggest that reactions of cyanide and phosphines with leinamycin produce the oxathiolanone intermediate (2), which is known to undergo rearrangement to the DNA-alkylating episulfonium ion 4.