Palladium‐Catalyzed Aminocarbonylation of Aryl Halides with 2,4,6‐Trichloro‐1,3,5‐triazine/Formamide Mixed Reagent

Abstract

In this work, the mixture of formamide and 2,4,6‐trichloro‐1,3,5‐triazine (cyanuric chloride or TCT) is introduced as a new amidating agent in Pd‐catalyzed aminocarbonylation of aryl halides. In the presence of a catalytic amount of palladium and TCT/formamide reagent, a range of aryl halides (X = Cl, Br, I) were converted into amides efficiently in N,N‐dimethylformamide at 120 °C.

Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts: New Entries to Aromatic Amides

“…These strategies were predominately used for the construction of aromatic amides with different substituents on the nitrogen atom. Another method was developed that is based upon the transition-metal-catalyzed arylation of N-substituted formamides by different aryl-containing reagents, predominantly aryl halides [ 32 , 33 , 34 ].…”

TBHP-mediated highly efficient dehydrogenative cross-oxidative coupling of methylarenes with acetanilides

“…What is more, the amide motif has also served as pivotal intermediate to generate several other organic functionalities [8–9]. To date, a large number of amidation reactions have been established [10–11], such as the condensation of carboxylic acid derivatives with amines [12], the rearrangement of ketoximes [13], the C–N cross coupling between aromatic amides or amines and aryl(pseudo)halides [14–15] or aldehydes [16–20]. However, to the best of our knowledge, the studies of dehydrogenative cross-oxidative-coupling reactions between methylarenes and amines for the formation of amides are rather limited, and which would be an important complement to the conventional C–N forming strategies.…”

Silylcarboxylic Acids as Bifunctional Reagents: Application in Palladium‐Catalyzed External‐CO‐Free Carbonylative Cross‐Coupling Reactions

“…Previously, phenyl formate and DMF have been utilized for formal alkoxy-and aminocarbonylations, but these reactions do not involve release of CO (Scheme 1c). [15,16] To date, our previous report involving external gaseous CO 2 is the only example of catalytic ketone formation employing a dual role CO precursor.…”

“…en-tries[13][14][15][16][17][18][19]. Employing dimethyl(phenyl) silanecarboxylic acid 4 instead of 2 a retarded the transformation(Table 1, entry 20).…”