Buchwald-Hartwig coupling

John F. Hartwig, one of the discoverers of the Buchwald-Hartwig coupling.

The Buchwald-Hartwig coupling is a reaction from the field of organic chemistry . It was developed in 1994 by the groups around John F. Hartwig and Stephen L. Buchwald . The reaction describes the palladium-catalyzed coupling of an aryl halide or triflate with a primary or secondary amine in the presence of a base.

Palladium complexes are used as the catalyst (M = Pd), the ligands (L) mostly being phosphines . Tris (dibenzylideneacetone) dipalladium (0) is also used as a catalyst. Bis (trimethylsilyl) amides or tert-butanolates are mostly used as bases .

literature

Ian Mangion: Buchwald-Hartwig Chemistry. MacMillan Group Meeting, July 30, 2002 (PDF; 928 kB )

Web links

Commons : Buchwald-Hartwig-coupling - collection of pictures, videos and audio files

Individual evidence

↑ Frederic Paul, Joe Patt, John F. Hartwig: Palladium-Catalyzed Formation of Carbon-Nitrogen Bonds. Reaction Intermediates and Catalyst Improvements in the Hetero Cross-Coupling of Aryl Halides and Tin Amides. In: Journal of the American Chemical Society . Volume 116, No. 13, 1994, pp. 5969-5970, doi: 10.1021 / ja00092a058 .
↑ Anil S. Guram, Stephen L. Buchwald: Palladium-Catalyzed Aromatic Aminations with in situ Generated Aminostannanes. In: Journal of the American Chemical Society. Volume 116, No. 17, 1994, pp. 7901-7902, doi: 10.1021 / ja00096a059 .
↑ John P. Wolfe, Stephen L. Buchwald: PALLADIUM-CATALYZED AMINATION OF ARYL HALIDES AND ARYL TRIFLATES: N-HEXYL-2-METHYL-4-METHOXYANILINE AND N-METHYL-N- (4-CHLOROPHENYL) ANILINE In: Organic Syntheses . 78, 2002, p. 23, doi : 10.15227 / orgsyn.078.0023 ; Coll. Vol. 10, 2004, p. 423 ( PDF ).

[1] Frederic Paul, Joe Patt, John F. Hartwig: Palladium-Catalyzed Formation of Carbon-Nitrogen Bonds. Reaction Intermediates and Catalyst Improvements in the Hetero Cross-Coupling of Aryl Halides and Tin Amides. In: Journal of the American Chemical Society . Volume 116, No. 13, 1994, pp. 5969-5970, doi: 10.1021 / ja00092a058 .

[2] Anil S. Guram, Stephen L. Buchwald: Palladium-Catalyzed Aromatic Aminations with in situ Generated Aminostannanes. In: Journal of the American Chemical Society. Volume 116, No. 17, 1994, pp. 7901-7902, doi: 10.1021 / ja00096a059 .

[3] John P. Wolfe, Stephen L. Buchwald: PALLADIUM-CATALYZED AMINATION OF ARYL HALIDES AND ARYL TRIFLATES: N-HEXYL-2-METHYL-4-METHOXYANILINE AND N-METHYL-N- (4-CHLOROPHENYL) ANILINE In: Organic Syntheses . 78, 2002, p. 23, doi : 10.15227 / orgsyn.078.0023 ; Coll. Vol. 10, 2004, p. 423 ( PDF ).