Preparation and Evaluation of Sterically Hindered Acridine Photocatalysts

Abstract

A practical nickel‐catalyzed protocol for the synthesis of sterically hindered 9‐arylacridines via Negishi type cross‐coupling was developed. The method enables a convenient approach to a set of active acridine photocatalysts starting from commercially available 9‐chloroacridine, inexpensive catalyst [NiCl2(Ph3P)2], and organozinc reagent with no need for additional ligands and precious metals. The synthetic protocol could be readily performed on a gram scale. The photocatalytic efficiency of obtained acridines was tested in decarboxylative thiolation and amination reactions. Structures of 19 acridines were studied by X‐ray analysis, which allowed to propose a steric descriptor relevant to the catalytic activity.

Degradation of Polyacrylates by One-Pot Sequential Dehydrodecarboxylation and Ozonolysis

“…27 This was likely due to the higher turnover efficiency of A2. 63 During dehydrodecarboxylation, the carboxylic acid of the chain transfer agent was converted into an alkene, while the trithiocarbonate was unchanged (Figures S18 and S19).…”

“…Gratifyingly, use of A2 instead of unsubstituted acridine led to disappearance of the small high molecular weight shoulder, likely due to coupling, that was present in the GPC trace of the decarboxylated MAA copolymer (P­(MA- co -MAA) 22% ) that was previously reported (Figures S17 and S34). This was likely due to the higher turnover efficiency of A2 . During dehydrodecarboxylation, the carboxylic acid of the chain transfer agent was converted into an alkene, while the trithiocarbonate was unchanged (Figures S18 and S19).…”

A sequential Friedländer and anionic benzannulation strategy for the regiodefined assembly of unsymmetrical acridines

“…1). 3 In addition, acridine-based dyes and pigments, 4 semiconductors, 5 fluorescent materials, 6 organic light-emitting diodes (OLEDs), 7 nanostructured photobasic units 8 and photoredox catalysts 9 have been extensively studied in recent years due to their impressive photophysical and photochemical properties. Therefore, the construction of acridine cores and preparation of acridine derivatives have received much attention from the synthetic community in recent years.…”

Dual Acridine/Decatungstate Photocatalysis for the Decarboxylative Radical Addition of Carboxylic Acids to Azomethines

“…As photocatalyst, acridine A1 bearing a 2,4,6-triisopropylphenyl group was optimal, as bulky groups of the ortho position of 9-aryl substituent decrease the photocatalyst degradation. 21 As a cocatalyst, TBADT (1 mol %) was added. In the absence of TBADT, incomplete conversion of the Schiff base was observed (entry 4).…”