Highly selective room-temperature copper-catalyzed C-N coupling reactions.
Through the use of cyclic beta-diketones as supporting ligands, the copper-catalyzed coupling of aryl iodides with aliphatic amines occurs at room temperature in as little as 1 h. These high reaction rates allow for the coupling of a wide range of aryl and heteroaryl iodides at room temperature. This method is highly tolerant of a number of reactive functional groups, including -Br and aromatic -NH2 as well as phenolic and aliphatic -OH. The high selectivity of the CuI-beta-diketone catalyst for aliphatic amines represents a useful complement to the palladium-based methods.
Shafir
Alexandr
A
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Buchwald
Stephen L
SL
D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature
D000588:Amines; D006846:Hydrocarbons, Halogenated; D008024:Ligands; D003300:Copper