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
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.
N,N-Dimethyl-β-alanine as an Inexpensive and Efficient Ligand for
Palladium-Catalyzed Heck Reaction
X. Cui, Z. Li, C.-Z. Tao, Y. Xu, J. Li, L. Liu, Q.-X. Guo, Org. Lett., 2006, 8, 2467-2470.
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.
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.
