Heterogeneous Thiocyanation of Benzylic Alcohols and Silyl and THP Ethers,and Deprotection of Silyl and THP-Ethers by [PCl3-n(SiO2)n] (Silphos)

Silicaphosphite (silphos), [PCl_3-n(SiO₂)_n], as a heterogeneous phosphorous compound, catalyzes the thiocyanation of benzylic alcohols and silyl and THP ethers in the presence of I₂ and NH₄SCN in refluxing CH₃CN. The produced silphos oxide byproduct can be easily separated by a simple filtration. Silphos is also used for the efficient and selective deprotection of silyl and THP-ethers to their corresponding alcohols.     

Heteropoly Acids as Heterogeneous and Reusable Catalyst for α-Thiocyanation of Ketones

Simple, efficient, and mild method for α-thiocyanation of ketones in presence of heteropolyacid has been developed. This methodology offered α-oxothiocyanates in good to excellent yields at room temperature in a highly selective manner. The catalyst could be efficiently recovered from the reaction and reused.     

Halogenation and thiocyanation of the univalent anion of dodecahydro-7,8-dicarba-nido-undecaborate in a diaphragm electrochemical cell

Iodination, bromination, and thiocyanation reactions of the potassium salt K⁺[7,8-C₂B₉H₁₂]^? are investigated during diaphragm electrolysis. The B(9)-monosubstituted derivatives [9-X-7,8-C₂B₉H₁₁]^? (X = I, SCN) and disubstituted derivatives [9,11-X₂-7,8-C₂B₉H₁₀]^? (X = Br, I) are obtained as alkylammonium salts. The composition and structure of these substances are confirmed by data from elemental analysis and IR and NMR (¹H and ¹¹B) spectroscopy.     

Electrochemical thiocyanation of dodecahydro-7,8-dicarba-<Emphasis Type="Italic">nido</Emphasis>-undecaborate and 7,8-dimethyldecahydro-7,8-dicarba-<Emphasis Type="Italic">nido</Emphasis>-undecaborate monoanions

Electrochemical thiocyanation of the dodecahydro-7,8-dicarba-nido-undecaborate and 7,8-dimethyldecahydro-7,8-dicarba-nido-undecaborate monoanions afforded thiocyanate derivatives of these compounds, which were isolated as alkylammonium salts. The structures of the synthesized compounds were determined by the data from IR, ¹H and ¹¹B NMR, and ¹¹B-¹¹B NMR COSY spectroscopy. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1553–1556, July, 2005.     

A rapid,mild, and efficient method for C-5 iodination/thiocyanation of 2-aminothiazoles

An efficient, green, rapid multitasking protocol for the selective C-5 substitution of 2-aminothiazole using iodic acid and aqueous PEG-400 was developed. The method found suitable for C-5 substitution i.e. iodination and thiocyanation of 2-amino thiazole using iodine and ammonium thiocyanate respectively. Iodic acid was found to be a good oxidant and aqueous PEG-400 as green reaction solvent.     

Transition-metal-free synthesis of thiocyanato- or nitro-arenes through diaryliodonium salts

A transition-metal-free approach to facile synthesis of thiocyanato- and nitro-arenes was developed from KSCN (potassiumthiocyanate) or NaNO₂ with 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.     

Facile Method for Thiocyanation of Activated Arenes Using Iodic Acid in Combination with Ammonium Thiocyanate

A facile method for direct thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate is described.     

Efficient Thiocyanation of Indoles Using Para-Toluene Sulfonic Acid

Treatment of indoles with ammonium thiocyanate in the presence of para-toluene sulfonic acid afforded the corresponding 3-thiocyano indoles at room temperature in excellent yields.     

Poly[4-diacetoxyiodo] Styrene–Promoted Thiocyanation of Aromatic Ethers,Anilines, and Indoles

Abstract

Thiocyanation of aromatic ethers, anilines, and indoles have been achieved using ammonium thiocyanate in the presence of poly[4-diacetoxyiodo] styrene (PDAIS) in CH₃CN at room temperature.

GRAPHICAL ABSTRACT