Direct C–H bond arylation of 2-hydroxybenzaldehydes with arylboronic acids via ligand-free palladium catalysis

Triphenylphosphinopalladium(II) complexes with ONO‐donor ligands: syntheses, structures and catalytic applications in CC cross‐coupling reactions

“…Though some palladium‐catalysed coupling reactions of arylboronic acids with aromatic aldehydes for the synthesis of diaryl ketones have been reported, a direct comparison of 1 , 2 , 3 with the catalyst systems reported earlier is difficult due to the differences in the reaction conditions such as solvent, base, temperature, reaction time and catalyst loading. However, in terms of the obtained yields, the efficiencies of the present palladium(II) complexes are comparable or slightly superior to those reported in the literature.…”

“…Examples for such palladium‐catalysed coupling reactions of arylboronic acids with aromatic aldehydes for the synthesis of diaryl ketones are very few. To the best of our knowledge, there have been only three reports so far . A one‐pot palladium‐catalysed coupling reaction of aryl aldehydes and organoboronic acids in the presence of P(1‐nap) 3 and Cs 2 CO 3 in toluene under aerobic conditions provided diaryl ketones in moderate to excellent yields .…”

“…A one‐pot palladium‐catalysed coupling reaction of aryl aldehydes and organoboronic acids in the presence of P(1‐nap) 3 and Cs 2 CO 3 in toluene under aerobic conditions provided diaryl ketones in moderate to excellent yields . A mild but efficient route for the preparation of 2‐hydroxybenzophenone derivatives in high yields is reported to be the palladium‐catalysed coupling of 2‐hydroxyaryl aldehydes with arylboronic acids in O 2 atmosphere using NaHCO 3 as base and CuCl 2 as additive . Preparation of diaryl ketones from aromatic aldehydes and organoboronic acids has been also achieved via palladium‐catalysed 1,2‐addition and oxidation by aryl iodides .…”

Crystal structure and Hirshfeld surface analysis of 2-hydroxy-7-methoxy-1,8-bis(2,4,6-trichlorobenzoyl)naphthalene

“…o-Hydroxyaryl ketones are generally recognized to be important precursors in the preparation of valuable products such as drugs, cosmetics, dyes and pesticides (Choy & Kwong, 2013;Naeimi et al, 2014;Nimnual et al, 2015). The preparation methods reported include, for example, Fries rearrangement of phenolic esters (Murashige et al, 2011), acylation of benzoquinone and derivatives (Schiel et al, 2001), coupling reactions of nitriles with boronic acids (Zhou & Larock, 2004), direct C-H bond arylation of 2-hydroxybenzaldehydes (Lee & Yi, 2015;Weng et al, 2010), and microwave-assisted direct benzoylation of phenols under solvent-free or ionic liquid conditions (Tran et al, 2017). The neighbouring carbonyl and hydroxy groups contribute to the regio-and chemoselectivities in these reactions.…”

Copper-Catalyzed Arylation of Arylboronic Acids with Aldehydes

“…For the aldehydes, electron-withdrawing and electronrich aromatic aldehydes reacted with 2b and gave diaryl ketones (3bb-jb) with moderate to good yields (Table 3, entries [10][11][12][13][14][15][16][17][18]. Aldehydes such as 1e, 1f, and 1g reacted well with 2a, and the products 3ea, 3fa, and 3ga were isolated in 88%, 67%, and 61% yields, respectively (Table 3, entries 13-15).…”