Recent Advances on Copper-Catalyzed C–C Bond Formation via C–H Functionalization

Abstract

Reactions that form C–C bonds are at the heart of many important transformations, both in industry and in academia. From the myriad of catalytic approaches to achieve such transformations, those relying on C–H functionalization are gaining increasing interest due to their inherent sustainable nature. In this short review, we showcase the most recent advances in the field of C–C bond formation via C–H functionalization, but focusing only on those methodologies relying on copper catalysts. This coinage metal has gained increased popularity in recent years, not only because it is cheaper and more abundant than precious metals, but also thanks to its rich and versatile chemistry.1 Introduction2 Cross-Dehydrogenative Coupling under Thermal Conditions2.1 C(sp3)–C(sp3) Bond Formation2.2 C(sp3)–C(sp2) Bond Formation2.3 C(sp2)–C(sp2) Bond Formation2.4 C(sp3)–C(sp) Bond Formation3 Cross-Dehydrogenative Coupling under Photochemical Conditions3.1 C(sp3)–C(sp3) Bond Formation3.2 C(sp3)–C(sp2) and C(sp3)–C(sp) Bond Formation4 Conclusion and Perspective

Recent developments on microwave-assisted organic synthesis of nitrogen- and oxygen-containing preferred heterocyclic scaffolds

“…Wang and co-workers discovered a novel, environmentally friendly synthetic route for the Friedländer quinoline synthesis of various substituted quinolines. 75 They performed the reaction with 2-aminobenzophenone 71 and various dicarbonyl moieties 72a–k using Nafion NR50 as a catalyst in ethanolic solvent under microwave conditions at 200 °C for 60 min to afford good isolated yields (43–95%) of polysubstituted quinolines 73a–k ( Scheme 24 ).…”

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

“…Sporadic examples using copper as transition metal for C-H functionalization reactions in combination with photocatalysis were also reported in the literature. The key advantages of the use of Cu as catalyst are related to its great abundance, as well as its cheap and non-toxic character [14,96,97].…”

Iron-Catalyzed Annulation of 2-Aminobenzaldehydes with Iodonium Ylides: A Mild and General Route for the Synthesis of Acridinone Derivatives

“…Nitrogen-containing benzo-fused heterocycles are one of the most important and attractive class of heterocycles, which are comprehensively present as core structural skeletons in various biologically relevant alkaloids and natural products [1][2][3]. Acridine and acridine-1-one derivatives are nitrogencontaining pivotal heterocyclic scaffolds ubiquitously present in a wide library of life-saving drug molecules such as anticancer, anti-Alzheimer, cholinesterase inhibitors, etc.…”