Iron‐Catalyzed Minisci Type Acetylation of N‐Heteroarenes Mediated by CH(OEt)₃/TBHP

Abstract

Iron‐catalyzed acetylation of electron deficient N‐heteroarenes has been reported using triethylorthoformate as robust and inexpensive acetyl source. This new method is successfully applied for the acetylation of quinolines, isoquinoline, quinoxalines, arylpyridines, bipyridines, and benzothiazole.

Philicity of Acetonyl and Benzoyl Radicals: A Comparative Experimental and Computational Study

“…[6,7] Although we observed that no reaction occurredw ith ketonederived radicals such as 2,s uccessful Minisci reactions with benzoyl and acyl radicals have been reported. [8] This increased our interest in the philicityo ft hese radicals, andh ow it affects reactions like those shown in Scheme1.…”

Green Approach for Visible-Light-Induced Direct Functionalization of 2-Methylquinolines

“…We then evaluated a blue light-emitting diode (LED) and a white compact fluorescent light (CFL) (entries 2 and 3) as sources of irradiation after 48 h, and compound 3aa was obtained in 23 and 26% yield, respectively. Doubling the amount of Lewis acid improved the yield to 48%, along with the C4-acylated byproduct 4 in 12% yield (entry 4). , Other solvents, such as 2-Me-THF, nitromethane, and ethanol, were evaluated but did not provide the desired product 3aa , while acetonitrile furnished compound 4 as the major product (entries 5–8). We observed that a more concentrated reaction mixture, which potentially favors the diffusion of the radicals, increased the yields of both 3aa and 4 to 58 and 20%, respectively (entry 9).…”

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

“…In this regard, the use of simple thiourea as an inexpensive thiocarbonyl group source in the multicomponent reaction with aldehydes and other reactive intermediates for the preparation of various triazinethione derivatives by independently varying the individual components thus represents a significant extension in this area. On the other hand, trialkyl orthoformates are versatile building blocks in organic synthesis, capable of constructing acyl derivatives [29][30][31][32][33] and ether derivatives [34][35][36] through acylation and alkylation under the appropriate conditions.…”