An efficient, one-pot strategy with high selectivity and high atom economy for the synthesis of o-aminobenzamides has been developed via palladium-catalyzed ortho-selective C-H oxidative carbonylation of N-substituted anilines with CO and primary amines. A wide range of N-substituted anilines and primary amines can be tolerated in this transformation to afford the corresponding o-aminobenzamides in moderate to excellent yields under mild conditions.
A new, selective protocol for the synthesis of 1-substituted 2-(trifluoromethyl)indoles has been developed by palladium-catalyzed double amination reaction of 2-chloro-1-(2-halophenyl)-3,3,3-trifluoroprop-1-enes with primary amines. This route allows the formation of two C-N bonds in one pot from the reaction between 2-chloro-1-(2-halophenyl)-3,3,3-trifluoroprop-1-enes and primary amines using the Pd 2 (dba) 3 /L4/t-BuONa system.
Synthesis of 1-Substituted 2-(Trifluoromethyl)indoles via a Palladium-Catalyzed Double Amination Reaction. -The new, practical process starts from o-halophenyl--substituted substrates (I) and (IV) and allows the formation of 2 C-N bonds in one pot. -(DONG, S.-X.; ZHANG*, X.-G.; LIU, Q.; TANG, R.-Y.; ZHONG, P.; LI, J.-H.; Synthesis 2010, 9, 1521-1525,
A facile, phosgene-free approach with high atom economy has been developed for the synthesis of N-aryl-N′-(4-pyridinyl)ureas. With cheap selenium as the catalyst, carbon monoxide (instead of phosgene) as the carbonyl reagent, N-aryl-N′-(4-pyridinyl)ureas can be obtained in a one-pot manner mostly in moderate to good yields via oxidative cross-carbonylation of 4-aminopyridine with a variety of aromatic amines in the presence of oxygen under atmospheric pressure. The mechanism for the synthesis of N-aryl-N′-(4-pyridinyl)ureas is also proposed.
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