Triethanolamine-based deep eutectic solvent as a novel, biocompatible, reusable, and efficient dual catalyst/solvent media for the selective tosylation and mesylation of phenols

Efficient base- and ligand-free palladium catalysed O -arylation of phenols in choline chloride:triethanolamine as a reusable deep eutectic solvent

“…After the completion of identification testing for the DES and ensuring the formation of DES, this catalyst was used for coupling of 1-iodo-4-nitrobenzene with phenolic derivatives. To determine the optimal conditions for this reaction, various DESs derived from ChCl or N -benzyl-2-hydroxy- N , N -dimethylethan-1-aminium chloride (NBHDMACl) [ 30 ] as the HBA and different HBDs such as urea, thiourea, glycerol, TEA, benzoic acid (BA) and metal halides (MCl) (M = Fe, Zn, Sn, Ni and Cu) were evaluated ( table 2 , entries 1–20). The results indicate that the best yield was achieved with the [ChCl][TEA] 2 DES ( table 2 , entry 4).…”

“…Also, when choline chloride is present alone, the desired reaction does not occur at all (table 2, entry 27). Subsequently, different amounts of the [ChCl][TEA] 2 solvent/catalyst system were tested (table 2, entries [28][29][30][31]. The effect of palladium as a catalyst was also investigated, revealing that no product was formed in its absence (table 2, entries 32-34), and the best efficiency was achieved with 0.006 g of the catalyst (table 2, entry 4).…”

Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)

“…Regarding to special features of deep eutectic solvents (DESs) as a class of ionic liquids 76 such as low vapor pressure, biodegradable and environmentally friendly systems, easy atom economic preparation, and excellent chemical and thermal stability 77 , they have received a lot of attention over the last decade. Thus, within this context and our ongoing research in the application of DESs in organic chemistry 78 – 80 , we plan to employ [ChCl][ZnCl 2 ] 2 DES as a green solvent/catalyst system for the first time in the synthesis of carboxamides, such as formanilides, acetanilides (Fig. 3 ), and also urea derivatives (Fig.…”