Synthesis of 2′,4‐Diarylbenzophenones through Site‐Selective Suzuki–Miyaura Reactions of Bis(triflates) of 2′,4‐Dihydroxybenzophenones

Abstract

Palladium(0)‐catalyzed Suzuki cross‐coupling reactions of the bis(triflates) of 2′,4‐dihydroxybenzophenones afforded 2′,4‐diarylbenzophenones. The reactions proceeded with very good site selectivity in favour of the 4‐position.

Regioselective Suzuki-Miyaura Reactions of Aromatic Bis-triflates: Electronic versus Steric Effects

“…In contrast, both an electron-withdrawing benzoyl group and an electron-withdrawing ester moiety are located para and ortho, respectively, to C-2. 18,19 2-Aryl-5-(2-arylbenzoyl)benzoates 30, containing two different aryl groups, were obtained by the arylation of triflate 29 (60-72% yield).…”

“…A second cross-coupling at C-2 gave 2,4′-diarylbenzophenones 27 in 62-76% yield. 18 Carbon atom C-4′ (para to the keto moiety) is less sterically hindered than C-2 (ortho to the keto moiety). Both centers are similar from an electronic viewpoint.…”

“…In contrast, both an electron-withdrawing benzoyl group and an electron-withdrawing ester moiety are located para and ortho, respectively, to C-2. 18,19…”

Synthesis and Chemical Reactivity of 4‐Oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde

“…4‐Oxo‐4 H ‐1‐benzopyran‐3‐carboxaldehyde 1 underwent Michael–retro‐Michael–Mukaiyama‐aldol reaction with 1‐phenyl‐1,3‐bis(trimethylsiloxy)‐1,3‐butadiene derivative 96 in the presence of the Me 3 SiOTf to give hydroxylated bis(benzophenone) 97 and 98 in 27–44% yields (Scheme ).…”

Chemical insights into the synthetic chemistry of five-membered saturated heterocycles—a transition metal–catalyzed approach

“…Amino acids, such as histidine, tryptophan, and proline, as well as vitamins and synthetase precursors such as pyridoxine, riboflavin, thiamine, biotin, folic acid, and B12 are some of the most prevalent heterocycles ( Ali et al, 2009 ; Ullah et al, 2009 ). Not only are they part of the structural units of living organisms, they impart a huge array of biological and medicinal properties, including, but not limited to, antibacterial, antiviral, antifungal, anti-inflammatory, anti-oxidant, anti-HIV, anti-cancer, antidiabetic, antidepressant, anti-microbial, anti-malarial, anti-neoplastic, anti-tubercular, anti-histaminic, anticoagulant, anti-allergic, enzyme inhibitors, anesthetics, and immunomodulatory agents ( Nawaz et al, 2011 ; Nawaz et al, 2012 ). Further, they are also prominent in agrochemicals, the food industry (coloring and flavoring agents), copolymers, photostabilizers, fluorescents, and corrosion protection chemicals ( Langer et al, 2011 ; Song et al, 2022 ).…”