(2-Pyridyl)acetone-Promoted Cu-Catalyzed O-Arylation of Phenols with Aryl Iodides, Bromides, and Chlorides

Abstract

Employing (2-pyridyl)acetone as a new supporting ligand, the copper-catalyzed coupling reactions of aryl chlorides, aryl bromides, and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. This reaction displays great functional groups compatibility and excellent reactive selectivity.

CuBr/N,N‐Dimethylglycine‐Catalyzed Coupling Reaction of 2‐Chlorotrifluoroacetanilides with Phenols at Mild Conditions

“…Generally, both electron-rich and electron-deficient phenols were compatible with these reaction conditions, delivering the corresponding diaryl ethers with good to excellent yields (Entries [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Noteworthy is that some sterically hindered phenols, such as 2-substituted phenols and 2,4,6-trimethylphenol, also worked well to provide 3k-3n in about 70% yield (Entries 10-13).…”

“…[2][3][4] However, for less expensive aryl chlorides, ligand-effect has been found less effective and therefore their coupling reactions with nucleophiles still required higher temperatures to complete. [5][6][7] For examples, copper-catalyzed coupling of aryl chlorides and phenols only took place at 120-135 ℃ by using TMHD 5 or (2-pyridyl)acetone 6 as the ligand.…”

Aminophenols as Efficient Ligand for Copper-Catalyzed Ullmann-type Synthesis of Diaryl Ethers

“…The results also indicated that the steric hindrance in both aryl bromides and phenols had a influence on the coupling reaction (Table 4, entries 3, 4, 8, 13, 14, 26 and 19-23. For instance, the O-arylation of various substituted phenols and 2-bromotoluene gave only moderate to good product yields (41-79 %) ( Table 4, entries [19][20][21][22][23], and only 51% yield was obtained after 24 h under our standard reaction conditions when 2, 6-dimethylphenol coupled with iodobenzene (Table 4, entry 8).…”

Recyclable and reusable nano-CuFe2O4 catalyzed C-O cross-coupling

“…During the last decade tremendous research work has been carried out on copper catalyzed reactions and showed that certain additives in combination with copper source enhanced the reaction rate under mild reaction conditions. Thus neocuproine [32], tripod ligands [33], ethylene glycol diactate [34], 1-naphthoic acid [35], 2,2,6,6-tetramethyl heptane-3,5-dione [36], β-keto ester [37], triphenyl phosphine [38], 2-pyridyl acetone [39], were successfully employed as additives. It is thought that these additives increase the efficiency of the catalyst by increasing the solubility of the copper salts and by preventing their aggregation [40].…”