Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.

The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C-H bond and the formation of a new arene C-N bond. The substitution pattern of the carbazole product can be controlled by the design of the biaryl amide substrate, and the method is compatible with a variety of functional groups.

Twofold C-H functionalization: palladium-catalyzed ortho arylation of anilides.

The ortho arylation of anilides to form biphenyls via a twofold C-H functionalization/C-C bond-forming process is described. The oxidative coupling takes place in the presence of 5-10 mol % of Pd(OAc)2, 10-20 mol % of DMSO, and 4-11 equiv of the aryl substrate in TFA under an oxygen atmosphere. No metal-containing cocatalyst is required.

Synthesis of novel spinosyn A analogues by Pd-mediated transformations.

The concept of modern crop protection demands for a continuous supply of new or modified established pesticides to avoid the development of serious resistances. Recent reports on the insecticidal spinosyns 1 and 2 show that also this class of pest managing agents is increasingly exposed to the formation of resistances. The synthesis of new derivatives is therefore highly desirable.