Buchwald-Hartwig Cross Coupling Reaction

Palladium-catalyzed synthesis of aryl amines. Starting materials are aryl halides or pseudohalides (for example triflates) and primary or secondary amines.

The synthesis of aryl ethers and especially diaryl ethers has recently received much attention as an alternative to the Ullmann Ether Synthesis.

Newer catalysts and methods offer a broad spectrum of interesting conversions.

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Mechanism of the Buchwald-Hartwig Coupling

 

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Recent Literature

(IPr)Pd(acac)Cl: An Easily Synthesized, Efficient, and Versatile Precatalyst for C-N and C-C Bond Formation
N. Marion, E. C. Ecarnot, O. Navarro, D. Amoroso, A. Bell, S. P. Nolan, J. Org. Chem., 2006, 71, 3816-3821.

Synthesis of Bulky and Electron-Rich MOP-type Ligands and Their Applications in Palladium-Catalyzed C-N Bond Formation
X. Xie, T. Y. Zhang, Z. Zhang, J. Org. Chem., 2006, 71, 6522-6529.

Triazole-Based Monophosphine Ligands for Palladium-Catalyzed Cross-Coupling Reactions of Aryl Chlorides
Q. Dai, W. Gao, D. Liu, L. M. Kapes, X. Zhang, J. Org. Chem., 2006, 71, 3928-3934.

Bulky Alkylphosphines with Neopentyl Substituents as Ligands in the Amination of Aryl Bromides and Chlorides
L. L. Hill, L. R. Moore, R. Huang, R. Craciun, A. J. Vincent, D. A. Dixon, J. Chou, C. J. Woltermann, K. H. Shaughnessy, J. Org. Chem., 2006, 71, 4951-4955.

Cross-Coupling and Dehalogenation Reactions Catalyzed by (N-Heterocyclic carbene)Pd(allyl)Cl Complexes
O. Navarro, H. Kaur, P. Mahjoor, S. P. Nolan, J. Org. Chem., 2004, 69, 3173-3180.

Expedited Palladium-Catalyzed Amination of Aryl Nonaflates through the Use of Microwave-Irradiation and Soluble Organic Amine Bases
R. E. Tundel, K. W. Anderson, S. L. Buchwald, J. Org. Chem., 2006, 71, 430-433.

An Air and Thermally Stable One-Component Catalyst for the Amination of Aryl Chlorides
D. Zim, S. L. Buchwald, Org. Lett., 2003, 5, 2413-2415.

(t-Bu)2PNP(i-BuNCH2CH2)3N: New Efficient Ligand for Palladium-Catalyzed C-N Couplings of Aryl and Heteroaryl Bromides and Chlorides and for Vinyl Bromides at Room Temperature
Ch. V. Reddy, J. V. Kingston, J. G. Verkade, J. Org. Chem., 2008, 73, 3047-3062.

Use of Polymer-Supported Dialkylphosphinobiphenyl Ligands for Palladium-Catalyzed Amination and Suzuki-Reaktions
C. A. Parrish, S. L. Buchwald, J. Org. Chem., 2001, 66, 3820-3827.

(t-Bu)2PNP(i-BuNCH2CH2)3N: New Efficient Ligand for Palladium-Catalyzed C-N Couplings of Aryl and Heteroaryl Bromides and Chlorides and for Vinyl Bromides at Room Temperature
Ch. V. Reddy, J. V. Kingston, J. G. Verkade, J. Org. Chem., 2008, 73, 3047-3062.

A new reactivity pattern for vinyl bromides: cine-substitution via palladium catalysed C-N coupling/Michael addition reactions
M. C. Willis, J. Chauhan, W. G. Whittinham, Org. Biomol. Chem., 2005, 3, 3094-3095.

Significantly Improved Method for the Pd-Catalyzed Coupling of Phenols with Aryl Halides: Understanding Ligand Effects
C. H. Burgos, T. E. Barder, X. Huang, S. L. Buchwald, Angew. Chem. Int. Ed., 2006, 45, 4321-4326.