Heck Reaction
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 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.
One of the benefits of the Heck Reaction is its outstanding trans selectivity.
Mechanism of the Heck Reaction
Recent Literature
New N-Heterocyclic Carbene Palladium Complex/Ionic Liquid Matrix Immobilized
on Silica: Application as Recoverable Catalyst for the Heck Reaction
B. Karimi, D. Enders, Org. Lett., 2006,
8, 1237-1240.
Pd(quinoline-8-carboxylate)2 as 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.
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.
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
L. Zhou, L. Wang,
Synthesis, 2006, 2649-2652.
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-mBDPP-Catalyzed Regioselective Internal Arylation of Electron-Rich
Olefins by Aryl Halides
S. Liu, N. Berry, N. Thomson, A. Pettman, Z. Hyder, J. Mo, J. Xiao, J. Org. Chem., 2006, 71, 7467-7470.
The Heck Reaction of Electron-Rich Olefins with Regiocontrol by
Hydrogen-Bond Donors
J. Mo, J. Xiao, Angew. Chem. Int. Ed., 2006, 45, 4152-4157.
Heck Coupling with Nonactivated Alkenyl Tosylates and Phosphates: Examples
of Effective 1,2-Migrations of the Alkenyl Palladium(II) Intermediates
A. L. Hansen, J.-P. Ebran, M. Ahlquist, P.-O. Norrby, T. Skydstrup, Angew. Chem. Int. Ed., 2006, 45, 3349-3353.
A New Route to the Synthesis of (E)- and (Z)-2-Alkene-4-ynoates and Nitriles from
vic-Diiodo-(E)-alkenes Catalyzed by Pd(0) Nanoparticles in Water
B. C. Ranu, K. Chattopadhyay, Org. Lett., 2007,
9, 2409-2412.
Synthesis of 2-Vinylic Indoles and Derivatives via a Pd-Catalyzed Tandem
Coupling Reaction
A. Fayol, Y.-Q. Fang, M. Lautens, Org. Lett., 2006, 8, 4203-4206.
Heck Vinylations Using Vinyl Sulfide, Vinyl Sulfoxide, Vinyl Sulfone, or
Vinyl Sulfonate Derivatives and Aryl Bromides Catalyzed by a Palladium Complex
Derived from a Tetraphosphine
A. Battace, T. Zair, H. Doucet, M. Santelli,
Synthesis, 2006, 3495-3505.
