Electroreductive intermolecular coupling of phthalimides with aldehydes: application to the synthesis of alkylideneisoindolin-1-ones

Electroreductive Intermolecular Coupling of Coumarins with Benzophenones: Synthesis of 4-(2-Hydroxyphenyl)-5,5-diaryl-γ-butyrolactones, 2-(2,2-Diaryl-2,3-dihydrobenzofuran-3-yl)acetic Acids, and 4-(Diarylmethyl)coumarins

“…Recently, 3- and 4-substituted coumarin derivatives have been extensively investigated as pharmacologically active compounds, such as anticancer, anti-neurodegenerative, and antituberculous agents . Therefore, the synthesis of 3- and 4-substituted coumarins attracts much attention from the synthetic chemists. , On the other hand, electroreduction is one of the useful methods for the reductive coupling of carbonyl compounds, and we have reported the electroreductive cross-coupling of heterocycles, such as phthalimides, indoles, and uracils, with carbonyl compounds. In this context, we attempted the electroreductive cross-coupling of coumarins with carbonyl compounds since this type of reaction is previously unknown and expected to provide a new synthetic route to 4-subsutituted coumarin derivatives.…”

Electroreductive Coupling of Phthalimides with α,β-Unsaturated Carbonyl Compounds and Subsequent Acid-Catalyzed Rearrangement to 4-Aminonaphthalen-1-ols: Density Functional Theory Study of the Acid-Catalyzed Rearrangement of Ketene Silyl Acetals

“…Exceptionally, the electroreduction of 1a with 2d produced hydrodimer of 2d (Scheme ), because 2d is more reducible than 1a . From these CV data and our previously reported results of the electroreductive coupling of phthalimides, , the reaction mechanism of the electroreductive coupling of 1 with 2a can be presumed as shown in Scheme . First, carbanion A is formed by the two-electron transfer to 1a and O silylation with TMSCl.…”

“…The reductive coupling of phthalimides with carbonyl compounds is one of the promising methods for the synthesis of 3-substituted isoindoline-1-ones. To date, this type of reaction has been realized with SmI 2 , electroreduction, low-valent titanium, and Zn . In this context, we reported in 2009 the electroreductive intramolecular coupling of phthalimides with α,β-unsaturated carbonyl compounds (Scheme ).…”

Organocatalytic Asymmetric Transformations of 3-Substituted 3-Hydroxyisoindolinones

“…The Kise group built on this principle and reported electroreductive coupling of phthalimides with aldehydes in the presence of chlorotrimethylsilane and triethylamine. 21 The authors expanded this methodology to the reductive coupling of phthalimides with aldehydes and ketones by using low-valent titanium. 22 The latter reaction furnished two-and four-electron reduced products, 3-hydroxyisoindolinones and 3-alkylideneisoindolinones, which could be obtained selectively by controlling the reaction conditions.…”