Sonochemistry and Copper Catalysis: An Efficient Duo in the Synthesis of Chalcogenylindolizines

Abstract

Herein, we describe an efficient and selective Cucatalyzed CÀ H bond chalcogenation of the indolizine core, in the presence of DMSO and applying ultrasound irradiation as an alternative energy source. Under the optimal conditions, 3-sulfanylindolizines (16 examples) were prepared in moderate to good yields starting from diorganyl disulfides and 2-arylindolizines. When diphenyl diselenide was used, 1,3-bis (selanyl) indolizines (4 examples) were exclusively obtained in very good yields. The use of ultrasound irradiation makes the reaction faster and more selective when compared to conventional heating.

Oxidation Potential-Guided Electrochemical Radical–Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

“…The current electrochemical coupling method could employ sodium heteroarylsulfinate and alkylsulfinates to give the desired products 5zb and 5zd – 5ze without much compromise in yields. The current electrochemical synthesis of 3-sulfonylated indolizines represents the first direct sulfonylation of indolizines …”

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“…The reactions were conducted smoothly for 1.5 h in the presence of CuCl (15 mol%) to afford the desired products 26 in moderate to very good yields (Scheme 9). More recently, the authors have expanded the method for the synthesis of 1,3-bis(phenylselenyl)indolizines 26 through an ultrasound-promoted Cu(I)-catalyzed reaction between 2-phenylindolizine derivatives 25 and diphenyl diselenide 6b [35]. The reactions were conducted smoothly for 1.5 h in the presence of CuCl (15 mol%) to afford the desired products 26 in moderate to very good yields (Scheme 9).…”

Indolizine: A Promising Framework for Developing a Diverse Array of C−H Functionalized Hybrids

“…al. [63] reported chalcogenation of indolizines by CÀ H functionalisation via a copper catalysed reaction through ultrasonication. To optimize the reaction conditions 2-phenylindolizines (1 d) and diphenyldisulphide (97 b) were utilised as the substrates in DMSO in the presence of 60 % US amplitude.…”

“…Filipe Penteado et. al [63] . reported chalcogenation of indolizines by C−H functionalisation via a copper catalysed reaction through ultrasonication.…”