The scope of palladium-catalyzed, auxiliary-assisted direct arylation and alkylation of sp2 and sp3 C–H bonds of amine and carboxylic acid derivatives has been investigated. The method employs a palladium acetate catalyst, substrate, aryl, alkyl, benzyl, or allyl halide, and inorganic base in tert-amyl alcohol or water solvent at 100–140 °C. Aryl and alkyl iodides as well as benzyl and allyl bromides are competent reagents in this transformation. The picolinic acid auxiliary is used for amine γ-functionalization, and the 8-aminoquinoline auxiliary is used for carboxylic acid β-functionalization. Some optimization of base, additives, and solvent is required for achieving best results.

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Scope and Limitations of Auxiliary-Assisted, Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 C–H Bonds

Mild metal-free sequential dual oxidative amination of C(sp3)-H bonds: efficient synthesis of imidazo[1,5-a]pyridines.

A facile iodine-mediated decarboxylative cyclization from α-amino acids and N-heterocyclic carbaldehydes was developed By virtue of this method, a series of imidazo[1,5-a]N-heterocycles can be synthesized efficiently under mild conditions A tentative reaction mechanism was proposed based on the experimental results and previous reports

Natural α-Amino Acids Applied in the Synthesis of Imidazo[1,5-a]N-heterocycles under Mild Conditions

Versatile manganese-catalyzed C–H arylations on synthetically meaningful pyridines were accomplished with sustainable MnCl2 as the catalyst. The oxidative C–H functionalizations proved viable with a user-friendly and safe continuous flow setup by weak amide-assisted C–H cleavage via a facile C–H activation regime.

Manganese(II/III/I)-Catalyzed C–H Arylations in Continuous Flow

The direct sequential arylation reaction at the C3 and C1 positions of imidazo[1,5-a]pyridines with a variety of aryl iodides catalyzed by [Pd(phen)2](PF6)2 is described. The reaction of unsubstitu...

Direct Sequential C3 and C1 Arylation Reaction of Imidazo[1,5-a]pyridine Catalyzed by a 1,10-Phenanthroline-Palladium Complex

Microwave-assisted organic synthesis of 3-substituted-imidazo[1,5-a]pyridines

3-Substituted-imidazo[1,5-a]pyridines were conveniently synthesized in two steps from commercially available picolinic esters under microwave irradiation conditions.

Microwave‐Assisted Organic Synthesis of 3‐Substituted‐imidazo[1,5‐a]pyridines.

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Microwave-assisted organic synthesis of 3-substituted-imidazo[1,5-a]pyridines

Microwave‐Assisted Organic Synthesis of 3‐Substituted‐imidazo[1,5‐a]pyridines.