Aminocarbonylation (hydrazinocarbonylation) of iodoalkenes and iodoarenes

Pd(triNHC)‐catalyzed Double Carbonylation of Aryliodides With Amines: The Effect of triNHC Ligands

“…The palladium‐catalyzed carbonylation of amines with aryl halides has been intensively studied to form synthetically valuable α‐ketoamides; the choice of palladium catalysts and the reaction optimization were critical to selectivity forming α‐ketoamides 1–16 . Due to the abundance of α‐ketoamides in natural products and pharmaceuticals, 17 efficient and selective catalytic conditions for forming α‐ketoamides are attractive.…”

“…The palladium-catalyzed carbonylation of amines with aryl halides has been intensively studied to form synthetically valuable α-ketoamides; the choice of palladium catalysts and the reaction optimization were critical to selectivity forming α-ketoamides. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] Due to the abundance of α-ketoamides in natural products and pharmaceuticals, 17 efficient and selective catalytic conditions for forming α-ketoamides are attractive. Based on prior work regarding the carbonylative coupling of amines and aryl halides, the effect of ligands, bases, and CO pressure are key factors that control the selectivity of α-ketoamides over amides; the double carbonylation forms α-ketoamides, and amides are produced by a single CO insertion (Figure 1).…”

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

“…Since the discovery of the aminocarbonylation by Heck et al (“Heck-carbonylation”) [ 23 , 24 , 25 ], the use of a primary or secondary amine, carbon monoxide, and aryl/alkenyl halides (or their synthetic surrogates, aryl triflates, and alkenyl triflates) in the presence of palladium catalysts leads to carboxamides in great variety [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ]. Several α,β-unsaturated carboxamides and aryl carboxamides, using palladium-catalyzed aminocarbonylation as a key reaction, were recently synthesized in our laboratory [ 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 ]. Just to illustrate the most recent developments, the functionalization of aromatic N -heterocycles in aminocarbonylation should be mentioned [ 46 , 47 , 48 , 49 ].…”