Modified palladium-catalyzed regioselective ortho-arylation of sp2 C–H bond substrates with a low catalyst loading

Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions

“…A related Pd(OAc) 2 -catalyzed sp 2 C–H arylation was developed using stoichiometric AgOAc in conjunction with 2–9 equiv of Ar-I 72,75. This method has been applied to the arylation of substituted anilides,72 2-arylpyridines,75,76,77 benzoxazoles,75,78 and benzoic acid derivatives (Scheme 27 and eq.…”

“…This method has been applied to the arylation of substituted anilides,72 2-arylpyridines,75,76,77 benzoxazoles,75,78 and benzoic acid derivatives (Scheme 27 and eq. 30).…”

Palladium-catalyzed non-directed C–H bond arylation of difluorobenzenes and dichlorobenzenes bearing benzoxazole or benzothiazole

“…28,29 On other hand, benzoxazole unit has been employed as directing group for the regioselective C2 arylation of phenyl using a palladium catalyst in the presence of silver carbonate in trifluoroacetic acid ( Figure 2b). 30,31 A similar procedure was reported by Ding, Peng and coworkers for the direct C2 arylation of 2-arylbenzothiazole ( Figure 2c). 32 To the best of our knowledge, the reactivity of dihalogenophenyls bearing a benzoxazole or a benzothiazole as potential directing groups in palladium-catalyzed direct arylation has never been reported.…”

Room Temperature CH Activation and Cross‐Coupling of Aryl Ureas in Water

“…[1,2] Despite substantially increased attention to the field, typical reaction conditions still require high temperatures (> 120 8C) for insertion into aromatic C À H bonds, which can be viewed as a major drawback to this chemistry. [1,2] Despite substantially increased attention to the field, typical reaction conditions still require high temperatures (> 120 8C) for insertion into aromatic C À H bonds, which can be viewed as a major drawback to this chemistry.…”

“…Recently, Lloyd-Jones and Booker-Milburn have also found aryl ureas to be more active coupling partners for C À H functionalizations than other anilides. Pivaloylanilide 1 c has been reported as an effective directing group at 130 8C, [1,2,5] but gave a low yield under these room temperature conditions (run 3). Pivaloylanilide 1 c has been reported as an effective directing group at 130 8C, [1,2,5] but gave a low yield under these room temperature conditions (run 3).…”