Synthesis of Multiply Arylated Heteroarenes, Including Bioactive Derivatives, via Palladium-Catalyzed Direct C–H Arylation of Heteroarenes with (Pseudo)Aryl Halides or Aryliodonium Salts

Abstract

This review with 387 references covers the literature until the end of November 2013 on the synthesis of multiply arylated heteroarenes via highly selective palladium-catalyzed direct C-H arylation reactions of heteroarene derivatives with aryl halides or pseudohalides or aryliodonium salts. Particular attention has been made to describe the synthesis of biologically active compounds and substances that are privileged structural motifs in organic materials. The practicality, versatility, and limitations of the various developed arylation protocols are discussed.

Samarium(III) Triflate as an Efficient and Reusable Catalyst for the Facile Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles

“…To date, several methodologies have been explored for synthesizing substituted imidazole derivatives. This includes cross-coupling reactions, [3+2] cycloaddition reaction of nitroolefins and N-aryl benzamidines, and multicomponent cyclocondensation synthesis in the presence of various catalysts [11][12][13][14].…”

Synthesis of fully arylated (hetero)arenes

“…In recent decades, many synthesis methods of multiply arylated (hetero)arenes have been reported. 2 As a subclass of multiply arylated (hetero)arenes, fully arylated (hetero)arenes have also flourished as a unique structural class in functional organic materials and biologically active compounds (representative molecules are shown in Fig. 1B).…”

Direct and Regioselective Introduction of Acetals into Imidazoles at the 2‐Position by an Iridium‐Catalyzed Reaction with Formates in the Presence of Hydrosilanes

“…Among these synthetic methodologies, transition‐metal‐catalyzed direct C–H functionalization has attracted particular attention as an efficient tool for the synthesis of highly substituted imidazoles . Considerable efforts have been made to develop new methods for C–C bond formation with aryl and alkenyl halides or pseudohalides catalyzed by various transition‐metal complexes . The oxidative C(sp 2 )–H/C(sp 2 )–H coupling of imidazoles at the C2 position with aromatic compounds has also been reported .…”