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The palladium-catalyzed C-C coupling between aryl halides or vinyl halides and activated alkenes in the presence of a base is referred as the "Heck
p y
Reaction". Recent developments in the catalysts and reaction conditions have resulted in a much broader range of donors and acceptors being amenable to the Heck Reaction.
g y One of the benefits of the Heck Reaction is its outstanding trans selectivity.
Mechanism of the Heak Reaction
Recent Literature
●Trifunctional N,N,O-terdentate amido/pyridyl carboxylate Pd(II) complexes were highly active and stable phosphine-free catalysts for Heck and room-temperature Suzuki reactions with high turnover numbers.
M. L. Kantam, P. Srinivas, J. Yadav, P. R. Likhar, S. Bhargava,J. Org. Chem.,2009,74, 4882-4885.
●New N-Heterocyclic Carbene Palladium Complex/Ionic Liquid Matrix Immobilized on Silica: Application as Recoverable Catalyst for the Heck Reaction
pp y
B. Karimi, D. Enders,Org. Lett.,2006,8, 1237-1240.
●Pd(quinoline-8-carboxylate)
2as a Low-Priced, Phosphine-Free Catalyst for Heck and Suzuki
Reactions
X. Cui, J. Li, Z.-P. Zhang, Y. Fu, L. Liu, Q.-X. Guo,J. Org. Chem.,2007,72, 9342-9345.
Recent Literature
●Triethanolamine as an Efficient and Reusable Base, Ligand and Reaction Medium for Phosphane-Free Palladium-Catalyzed Heck Reactions
H. J. Li, L. Wang,Eur. J. Org. Chem.,2006, 5101-5102.
●Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction
A.-E. Wang, J.-H. Xie, L.-X. Wang, Q.-L. Zhou,Tetrahedron,2005,61, 259-266.
A E Wang J H Xie L X Wang Q L Zhou259266
p g p q
●Heck Couplings at Room Temperature in Nanometer Aqueous Micelles
B. H. Lipshutz, B. R. Taft,Org. Lett.,2008,10, 1329-1332.
Recent Literature
●Efficient Aqueous-Phase Heck and Suzuki Couplings of Aryl Bromides Using Tri(4,6-
dimethyl-3-sulfonatophenyl)phosphine Trisodium Salt (TXPTS)
L. R. Moore, K. H. Shaughnessy,Org. Lett.,2004,6, 225-228.
●Poly(ethylene glycol) (PEG) as a Reusable Solvent Medium for Organic Synthesis. Application in the Heck Reaction
S. Chandrasekhar, C. Narsihmulu, S. S. Sultana, N. R. Reddy,Org. Lett.,2002,4, 4399-4401.
●Functionalized Ionic Liquid as an Efficient and Recyclable Reaction Medium for Phosphine-Free Palladium-Catalyzed Heck Reaction
Palladium Catalyzed Heck Reaction
L. Zhou, L. Wang,Synthesis,2006, 2649-2652.
Recent Literature
●Brønsted Guanidine Acid-Base Ionic Liquids: Novel Reaction Media for the Palladium-
Catalyzed Heck Reaction
S. Li, Y. Lin, H. Xie, S. Zhang, J. Xu,Org. Lett.,2006,8, 391-394.
●Pd-m BDPP-Catalyzed Regioselective Internal Arylation of Electron-Rich Olefins by Aryl Halides
y y g
S. Liu, N. Berry, N. Thomson, A. Pettman, Z. Hyder, J. Mo, J. Xiao,J. Org. Chem.,2006,71, 7467-7470.
●Regioselective Heck Vinylation of Electron-Rich Olefins with Vinyl Halides: Is the Neutral Pathway in Operation?
in Operation?
M. McConville, O. Saidi, J. Blacker, J. Xiao,J. Org. Chem.,2009,74, 2692-2698.