Microwave-assisted reaction of aryl diazonium fluoroborate and diaryl dichalcogenides in dimethyl carbonate: a general procedure for the synthesis of unsymmetrical diaryl chalcogenides

Abstract

The simplicity in operation, general applicability to all three chalcogenides (III), (V) and (VII), use of recycable dimethyl carbonate and employment of stable and readily available dichalcogenides in place of thiols and analogues makes the procedure environmentally friendly and more cost‐effective.

Substituent Effects in Chain‐Breaking Aryltellurophenol Antioxidants

“…33–35 °C; 1 H NMR (400 MHz, CDCl 3 ): δ =7.82 (dd, J= 1.6, 7.6 Hz, 1 H), 7.51 (m, 2 H), 7.35 (td, J= 1.6, 7.6 Hz, 1 H), 7.24 (m, 1 H), 7.18 (m, 2 H), 7.09 (dd, J= 1.6, 8.0 Hz, 1 H), 6.82 (m, 1 H), 6.15 ppm (s, 1 H); 13 C NMR (100 MHz, CDCl 3 ): δ =157.5, 141.7, 135.9, 132.4, 129.7, 127.8, 121.8, 113.9, 113.8, 103.7 ppm; 125 Te NMR (126 MHz, CDCl 3 ): δ =425 ppm. The 1 H and 13 C NMR spectra were in accordance with the literature data …”

“…13 CNMR spectra were in accordance with the literature data. [27] Compound 7b: O-THP-2-bromophenol (342 mg, 1.3 mmol), tertbutyllithium (1.7 m,1 .5 mL, 2.6 mmol), bis-4-(methoxy)phenyl ditelluride (626 mg, 1.3 mmol), and p-toluenesulfonic acid monohydrate (45 mg, 0.24 mmol) were reacted according to the general procedure to give 7b as an orange solid (288 mg, 68 %). M.p.…”

Synthesis of Unsymmetrical Diorganyl Chalcogenides under Greener Conditions: Use of an Iodine/DMSO System, Solvent‐ and Metal‐Free Approach

“…Among them, metal‐catalyzed aryl‐chalcogen bond formation is one of the most commonly used protocols,2a–c,11 which generally involves the presence of a ligand. Several metal sources, such as Pd,12 Ni,13 Cu,14 Zn,15 Fe16 and In,17 have been used. However, these types of transformations have their own particular drawbacks, such as the use of environmentally unfriendly solvents, expensive ligands and catalysts, precious and rare metals, reducing agents, stoichiometric or greater amounts of reagents, long reaction times, harsh reaction conditions and oxygen‐free techniques.…”

Facile Synthesis of Tuneable Azophosphonium Salts

“…Synthesis of p ‐Isopropoxybenzenediazonium Tetrafluoroborate [ p ‐(CH 3 ) 2 HCO‐PhN 2 ][BF 4 ]: [ p‐i PrO‐PhN 2 ][BF 4 ] was synthesised using method A starting with 4‐isopropoxyaniline (0.35 mL, 2.4 mmol, 1.0 equiv), which afforded the crude product as a slightly purple powder in 93 % (555.9 mg, 2.224 mmol). During the synthesis an additional 1.5 mL of water was added to improve stirring.…”