Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism

John F Hartwig

doi:10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L

Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism

Angew Chem Int Ed Engl. 1998 Aug 17;37(15):2046-2067. doi: 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L.

Author

John F Hartwig¹

Affiliation

¹ Department of Chemistry, Yale University, PO Box 208107, New Haven, CT 06520-8107 (USA), Fax: (+1) 203-432-6144.

Abstract

Oxidative addition and reductive elimination are the central steps in new palladium-catalyzed chemistry that forms C-N and C-O bonds in arylamines and ethers. In the potential mechanism shown on the right the amine is formed by reductive elimination from a four-coordinate, 16-electron amido aryl complex. The use of a chelating ligand such as 1,1'-bis(diphenylphosphanyl)ferrocene (DPPF) reduces the occurrence of the competing β-hydrogen elimination. X=Br, I; R, R'=alkyl, aryl.

Keywords: Aminations; Arylations; Ethers; Nickel; Palladium.

Publication types

Review