Reductive silylation and alkylation of phthalimides

The Morita–Baylis–Hillman reaction for non-electron-deficient olefins enabled by photoredox catalysis

“…Based on the previous photoredox-quinuclidine dual catalysis, we selected Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6 (PC1) as the photocatalyst to oxidize quinuclidine and cyclopentene (1a) as the olefin partner to evaluate our working hypothesis. Fortunately, when using N-phenyl phthalimide (2a) with a higher reduction potential as the acceptor, [31][32][33][34][35] we obtained the desired product 3aa. Based on the initial investigation, we further optimized the reaction conditions (Table 1) and found that the reaction efficiency was not affected by increasing the loading of quinuclidine (entries 1-4).…”

Darstellung und Reaktionen von 2-Alkoxy-1,3-bis-(trimethylsilyloxy)-2 H-isoindolen/ Preparation and Reactions of 2-Alkoxy-1,3-bis-(trimethylsilyloxy)-2H-isoindoles

“…1-Alkoxy-isoindole liegen nur in einer tautom eren Form als lH -Isoindole vor [1], Wir konnten 1,3-Bis-(trimethylsilyloxy)-2 H-isoindole über die elektro chemische Reduktion von N-substituierten Phthalsäureimiden erstmals darstellen [2]. Vor kurzem beschrieb K reher die Synthese von l,3-Dimethoxy-2-methyl-2H-isoindol [3], Durch D onatorsubstituenten in den bereits im G rundkörper elektronenreichen 1-und 3-Positionen [4] wird das 2H -Isoindol zunehm end destabilisiert.…”