Pubblications Supported Eosin Y as a Photocatalyst for C-H Arylation of Furan in Batch and Flow S. Rossi, F. Herbrik, S. Resta, A. Puglisi Molecules, 2022 [Link] Abstract: Eosin Y is one of the most popular organic dyes used as a photoredox catalyst and is largely employed in photochemical reactions both as a homogeneous and heterogeneous photocatalyst after immobilization. Immobilization of Eosin Y onto a solid support has many advantages, such as the possibility of recovery and reuse of the photocatalyst and the possibility of its use under flow conditions. In this paper, we report our findings on the immobilization of Eosin Y onto Merrifield resin and its application in the direct photochemical arylation of furan with aryldiazonium salts. The synthesized supported photocatalyst was used in batch reactions under heterogeneous conditions with different aryl diazonium salts, and its recovery and recycle were demonstrated for up to three times. The immobilized photocatalyst was then loaded in a packed-bed reactor and used under continuous flow conditions. The flow reaction allowed the arylated products to be obtained with higher productivity and space-time-yield than the batch in a very short reaction time. Immobilized Eosin Y for the photocatalytic oxidation of tetrahydroisoquinolines in flow F. Herbrik, S. Rossi, M. Sanz, A. Puglisi, M. Benaglia ChemCatChem, 2022 [Link] Abstract: A straightforward synthetic strategy for the immobilization of Eosin Y onto Merrifield-resin was successfully developed. The easy-to-synthesize new material efficiently promoted the photooxidation of tertiary amines, especially operating with continuous flow catalytic reactors. When using the iminium-ions in situ or in a telescoped fashion the resulting Mannich-products could be isolated with high degrees of diastereo- and enantioselectivity (up to 90% e.e.), simply using air as terminal oxidant. The same reactor was reused several times, with no loss of efficiency and no apparent material degradation. Enantioselective organophotocatalytic telescoped synthesis of a chiral privileged active pharmaceutical ingredient F. Herbrik , M. Sanz, A. Puglisi, S. Rossi, M. Benaglia Chem. Eur. J. , 2022 [Link] Abstract: An efficient in-flow catalytic enantioselective organophotoredox alkylation of aldehydes has been successfully developed (up to 98% e.e.) and applied to the fully telescoped synthesis of a chiral active pharmaceutical ingredient (API), consisting of four units of operation: in-flow asymmetric benzylation, inline continuous work-up, neutralisation and oxidative amidation. By using flow technologies, the productivity was increased by almost 200 times compared to the batch reaction. Electrochemical Organic Synthesis of Electron-Rich Biaryl Scaffolds: An Update F. Medici, S. Resta, A. Puglisi, S. Rossi, L. Raimondi. M. Benaglia Molecules, 2021 26(22), 6968[Link] Abstract: Biaryl scaffolds are widely spread in biologically important natural products, in numerous therapeutic agents, but they are also considered a privileged class of ligands and (organo)catalysts; therefore, the development of efficient alternative methodologies to prepare such compounds is always attracting much attention. The present review discusses the organic electrosynthesis of biaryls starting from phenols, anilines, naphthols, and naphthylamines. The most significant examples of the works reported in the last decade are presented and classified according to the single class of molecules: after the introduction, the first three sections relate to the reactions of phenols, naphthols, and anilines, respectively; the other two sections refer to cross-coupling and miscellaneous reactions. Nitroalkene reduction in deep eutectic solvents promoted by BH3NH3 C. Faverio, M. Boselli, P. Camarero Gonzalez, A. Puglisi, M. Benaglia Beilstein J. Org. Chem, 2021 17, 1041–1047. [Link] Abstract: Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH3NH3, with bio-based eutectic mixtures as biorenewable solvents in the synthesis of nitroalkanes, valuable precursors of amines. A variety of nitrostyrenes and alkyl-substituted nitroalkenes, including α- and β-substituted nitroolefins, were chemoselectively reduced to the nitroalkanes, with an atom economy-oriented, simple and convenient experimental procedure. A reliable and easily reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated. In flow enantioselective homogeneous organic synthesis A. Puglisi, S. Rossi, F. Herbrik, F. Medici, M. Benaglia Green Processing and Synthesis, 2021 10, 1-11 [Link] Abstract: The use of enabling technologies, such as flow reactors, three-dimensional-printed devices, and electrochemistry, in the stereoselective synthesis of enantioenriched compounds is presented, with a special focus on the most significant contributions to the field reported in the last few years. Eosin Y: Homogeneous Photocatalytic In-Flow Reactions and Solid-Supported Catalysts for In-Batch Synthetic Transformations F. Herbrik, P. Camarero Gonzalez, M. Krstic, A. Puglisi, M. Benaglia, M.A. Sanz, S. Rossi Appl. Sci., 2020 [Link] Abstract: In this paper, the most recent and significant applications of Eosin Y as an organo-photocatalyst will be discussed, focusing the attention on enabling technological aspects in homogeneous photochemical flow reactions, as well as on recent developments in solid-supported catalyst applications for batch synthetic transformations.