Metal and base-free synthesis of arylselanyl anilines using glycerol as a solvent

Green alternative solvents for the copper-catalysed arylation of phenols and amides

“…The reaction of benzamide, 4-methoxy benzamide and 3-(trifluoromethyl)benzamide with electron-donating to electronwithdrawing aryl iodides occurred with good yields (25-32, 56% to 91% yields). Arylation of cyclohexanecarboxamide gave products 33-35 with yields between 71% and 78%, while cyclic amides such as 2-pyrrolidinone and 2-hydroxypyridine gave excellent results, with yields of 87-98% (36)(37)(38)(39)(40) [52][53][54] Benzylation also proved effective under these conditions: from the reaction of benzamide with 2-iodobenzyl bromide, a doubly substituted product was obtained in 30% yield (48, Scheme 5), while the coupling with benzyl bromide and benzyl chloride occurred with 52% and 33% yields respectively (49). It is worth noting that product 49 was not observed in reactions without CuI/ligand, either with benzyl bromide or benzyl chloride.…”

“…Other potentially interesting solvents have only been recently added to green solvent tables, being less established. 7 For example, glycerol and its derivatives have been found as good alternatives to other organic solvents in several processes, [35][36][37][38] and used in agrochemical formulations. 39 Derivatives of isosorbide, another naturally-derived compound, have been used as co-solvents or carriers in many pharmaceutical and cosmetic formulations, 40,41 thanks to their non-toxicity and favourable chemical properties.…”

An environmentally benign and efficient synthesis of 4‐Selanylpyrazoles catalyzed by haloid salts in water

“…of 1a with 1.0 equiv. for H 2 O 2 proved to be the best choices (entries 5, [16][17][18][20][21][22]. of oxidant H 2 O 2 and 15 mol% of NaCl in H 2 O for 6 hr at room temperature, the desired product, 3,5-dimethyl-1-phenyl-4--(phenylselanyl)-1H-pyrazole 3a was obtained in a good yield of 86% (Table 1, entry 1).…”

“…Then, the optimal amounts of NaBr and H 2 O 2 were evaluated respectively, and as a result, 15 mol% for NaBr and 2.0 equiv. for H 2 O 2 proved to be the best choices (entries 5, [16][17][18][20][21][22]. However, in the absence of NaBr or H 2 O 2 , 3a was not observed (entries 15 and 19).…”

“…The difunctionalizations of alkenes is a main procedure for the synthesis of organoselinides, [13][14][15][16][17][18] and the senelynation of electron-rich aromatic compounds is another normal method for obtaining organoselinides. [19][20][21][22][23][24][25][26][27] Despite organoselinides being important in biological activities and in organic synthesis, there are few studies reported on selanyl-substituted pyrazoles, a kind of heteroaryl selinides, and the number of those pyrazoles is limited. Fritsky's group first reported a procedure for the preparation of symmetrical selanyl-substituted pyrazoles with substituted pyrazoles and selenium dioxide in pyridine, which provided the corresponding products in moderate yields.…”