Further Information
Literature
Related Reactions
Stille Coupling
Alkenylations
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
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
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.
1,1'-Methylene-3,3'-bis[(N-(tert-butyl)imidazol-2-ylidene] and
Its Effect in Palladium-Catalyzed C-C Coupling
S. Nadri, E. Rafiee, S. Jamali, M. Joshaghani,
Synlett, 2015, 26, 619-624.
Heck Reactions Catalyzed by Ultrasmall and Uniform Pd Nanoparticles
Supported on Polyaniline
L. Yu, Y. Huang, Z. Wei, Y. Ding, C. Su, Q. Xu, J. Org. Chem.,
2015,
80, 8677-8683.
Efficient Heck Vinylation of Aryl Halides Catalyzed by a New Air-Stable
Palladium-Tetraphosphine Complex
M. Feuerstein, H. Doucet, M. Santelli, J. Org. Chem., 2001,
66, 5923-5925.
Highly Efficient Heck Reactions of Aryl Bromides with n-Butyl
Acrylate Mediated by a Palladium/Phosphine-Imidazolium Salt System
C. Yang, H. Man Lee, S. P. Nolan,
Org. Lett., 2001, 3, 1511-1514.
Screening of Homogeneous Catalysts by Fluorescence Resonance Energy
Transfer. Identification of Catalysts for Room-Temperature Heck Reactions
J. P. Stambuli, S. R. Stauffer, K. H. Shaughnessy, J. F. Hartwig, J. Am. Chem. Soc., 2001,
123, 2677-2678.
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.
An Efficient and General Method for the Heck and Buchwald-Hartwig Coupling
Reactions of Aryl Chlorides
D.-H. Lee, A. Taher, S. Hossain, M.-J. Jin, Org. Lett., 2011,
13, 5540-5543.
Palladium-Catalyzed Heck Reaction of Aryl Chlorides under Mild Conditions
Promoted by Organic Ionic Bases
H.-J. Xu, Y.-Q. Zhao, X.-F. Zhou, J. Org. Chem., 2011,
76, 8036-8041.
A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides
under Mild Conditions
A. F. Littke, G. C. Fu, J. Am. Chem. Soc., 2001,
123, 6989-7000.
Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room
Temperature
G.-Z. Wang, R. Shang, W.-M. Cheng, Y. Fu, J. Am. Chem. Soc., 2017,
139, 18307-18312.
Controlling Reactivity and Selectivity in the Mizoroki-Heck Reaction: High
Throughput Evaluation of 1,5-Diaza-3,7-diphosphacyclooctane Ligands
E. S. Isbrandt, D. E. Chapple, N. T. . Tu, V. Dimakos,
A. M. M. Beardall, P. D. Boyle, C. N. Rowley, J. M. Blacquiere, S. G. Newman, J. Am. Chem. Soc.,
2024, 146, 5650-5660.
Controlling Reactivity and Selectivity in the Mizoroki-Heck Reaction: High
Throughput Evaluation of 1,5-Diaza-3,7-diphosphacyclooctane Ligands
E. S. Isbrandt, D. E. Chapple, N. T. . Tu, V. Dimakos,
A. M. M. Beardall, P. D. Boyle, C. N. Rowley, J. M. Blacquiere, S. G. Newman, J. Am. Chem. Soc.,
2024, 146, 5650-5660.
Efficient Aqueous-Phase Heck Reaction Catalyzed by a Robust Hydrophilic
Pyridine-Bridged Bisbenzimidazolylidene-Palladium Pincer Complex
Z. Wang, X. Feng, W. Fang, T. Tu, Synlett, 2011,
951-954.
A palladacycle phosphine mono-ylide complex is as an efficient catalyst for
the Mizoroki-Heck cross-coupling reaction of aromatic or aliphatic olefins with
a broad range of aryl bromides and chlorides. The reactions proceeded in good
yields in the presence of low loadings of palladium (10 ppm) under aerobic
conditions. High catalyst activities with turnover frequencies of up to 20,000 h-1
were observed at 130°C.
S. J. Sabounchi, M. Ahmadi, T. Azizi, M. Panahimehr, Synlett, 2014, 25,
336-342.
An efficient and simple protocol for phosphine-free Heck reactions in water in
the presence of a Pd(L-proline)2 complex as the catalyst under
controlled microwave irradiation conditions is versatile and provides excellent
yields of products in short reaction times. The reaction system minimizes costs,
operational hazards and environmental pollution.
B. K. Allam, K. N. Singh, Synthesis, 2011,
1125-1131.
Heck Couplings at Room Temperature in Nanometer Aqueous Micelles
B. H. Lipshutz, B. R. Taft, Org. Lett., 2008,
10, 1329-1332.
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.
Brřnsted 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.
Practical Heck-Mizoroki Coupling Protocol for Challenging Substrates
Mediated by an N-Heterocyclic Carbene-Ligated Palladacycle
E. A. B. Kantchev, G.-R. Peh, C. Zhang, J. Y. Ying, Org. Lett.,
2008,
10, 3949-3952.
Mizoroki-Heck Type Reaction of Organoboron Reagents with Alkenes and
Alkynes. A Pd(II)-Catalyzed Pathway with Cu(OAc)2 as an Oxidant
X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata,
T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett., 2001,
3, 3313-3313.
A palladium-catalyzed decarbonylative alkenylation of various benzoic acids
with terminal alkenes provides the corresponding internal alkenes in very good
yields. The conversion of cinnamic acids and bioactive benzoic acids such as
3-methylflavone-8-carboxylic acid, probenecid, adapalin, and febuxostat
demonstrate the synthetic value of this new reaction.
W. Yu, L. Liu, T. Huang, X. Zhou, T. Chen,
Org. Lett., 2020, 22, 7123-7128.
Chiral-Anion-Mediated Asymmetric Heck-Matsuda Reaction of Acyclic Alkenyl
Alcohols
T. Zhang, W.-A. Li, H.-C. Shen, S.-S. Chen, Z.-Y. Han, Org. Lett., 2021, 23,
1473-1477.
A Sustainable Procedure Combining the Advantages of Both Homogeneous and
Heterogeneous Catalysis for the Heck-Matsuda Reaction
C. Rossy, E. Fouquet, F.-X. Felpin, Synthesis, 2012, 44,
37-41.
Operationally Simple and Highly (E)-Styrenyl-Selective Heck Reactions
of Electronically Nonbiased Olefins
E. W. Werner, M. S. Sigman, J. Am. Chem. Soc., 2011,
133, 9692-9695.
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.
Regioselective Heck Vinylation of Electron-Rich Olefins with Vinyl Halides:
Is the Neutral Pathway in Operation?
M. McConville, O. Saidi, J. Blacker, J. Xiao, J. Org. Chem., 2009,
74, 2692-2698.
Heck Reaction of 2-Oxyacrylates with Aryl Bromides: A Common Route to
Monoaryl Pyruvates and Ortho Ester-Protected Monoaryl Pyruvates
K. Matcha, K. Chernichenko, K. Jouvin, S. B. Guduguntla, D. N. Tran, S. Bell,
W. Paden, M. Figlus, C. Muir, C. H. Diaz, J. Org. Chem., 2022, 87,
10736-10746.
Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C
Bond Olefination
M.-L. Wang, H. Xu, H.-Y. Li, B. Ma, Z.-Y. Wang, X. Wang, H.-X. Dai, Org. Lett., 2021, 23,
2147-2152.
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.
Palladium-Tetraphosphine Complex Catalysed Heck Reaction of Vinyl Bromides
with Alkenes: A Powerful Access to Conjugated Dienes
M. Lemhadri, A. Battace, F. Berthiol, T. Zair, H. Doucet, M. Santelli, Synthesis, 2008,
1142-1152.
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.
"Bulky-Yet-Flexible" α-Diimine Palladium-Catalyzed Reductive Heck
Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in
Air
X.-W. Yang, D.-H. Li, A.-X. Song, F.-S. Liu, J. Org. Chem., 2020, 85,
11750-11765.
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.
A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and
1,3,5-Triene Synthesis through C-C Bond Scission
N. J. McAlpine, L. Wang, B. P. Carrow, J. Am. Chem. Soc.,
2018,
140, 13634-13639.
Direct Acylation of Aryl Bromides with Aldehydes by Palladium Catalysis
J. Ruan, O. Saidi, J. A. Iggo, J. Xiao, J. Am. Chem. Soc., 2008,
130, 10510-10511.
Merging of Light/Dark Palladium Catalytic Cycles Enables Multicomponent
Tandem Alkyl Heck/Tsuji-Trost Homologative Amination Reaction toward Allylic
Amines
N. Kvasovs, J. Fang, F. Kliuev, V. Gevorgyan, J. Am. Chem. Soc.,
2023, 145, 18497-18505.
Preparation of Vinyl Silyl Ethers and Disiloxanes via the Silyl-Heck
Reaction of Silyl Ditriflates
S. E. S. Martin, D. A. Watson, J. Am. Chem. Soc., 2013,
135, 13330-13333.
Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A
Boryl-Heck Reaction
W. B. Reid, J. J. Spillane, S. B. Krause, D. A. Watson, J. Am. Chem. Soc., 2016,
138, 5539-5542.
Synthesis of Trisubstituted Alkenyl Boronic Esters from Alkenes Using the
Boryl-Heck Reaction
W. B. Reid, D. A. Watson, Org. Lett.,
2018, 20, 6822-6826.
Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of
Aliphatic N-(Acyloxy)phthalimides at Room Temperature
G.-Z. Wang, R. Shang, Y. Fu, Org. Lett.,
2018, 20, 888-891.
Synthesis of Arylidene-β-lactams via exo-Selective Matsuda-Heck
Arylation of Methylene-β-lactams
N. Riemer, M. Riemer, M. Krüger, G. J. Clarkson, M. Shipman, B. Schmidt, J. Org. Chem., 2021, 86,
8786-8796.
A Redox-Relay Heck Approach to Substituted Tetrahydrofurans
T. J. M. Byrne, M. E. Mylrea, J. D. Cuthbertson, Org. Lett., 2023, 25,
2361-2365.
Asymmetric Intermolecular Heck Reaction of Aryl Halides
C. Wu, J. Zhou, J. Am. Chem. Soc., 2014,
136, 650-652.
Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
M. R. Harris, M. O. Konev, E. R. Jarvo, J. Am. Chem. Soc., 2014,
136, 7825-7828.
Asymmetric Domino Heck Arylation and Alkylation of Nonconjugated Dienes:
Double C–F···Sodium Attractive Noncovalent Interaction
D. Zhu, W. Xu, M. Pu, Y.-D. Wu, Y. R. Chi, J. S. Zhou, Org. Lett., 2021, 23,
7064-7068.
Palladium-Catalyzed 6-Endo Selective Alkyl-Heck Reactions: Access to
5-Phenyl-1,2,3,6-tetrahydropyridine Derivatives
X. Dong, Y. Han, F. Yan, Q. Liu, P. Wang, K. Chen, Y. Li, Z. Zhao, Y. Dong, H.
Liu, Org. Lett.,
2016, 18, 3758-3761.
Domino Sequences Involving Stereoselective Hydrazone-Type Heck Reaction and
Denitrogenative [1,5]-Sigmatropic Rearrangement
S. Yu, L. Zhou, S. Ye, X. Tong, J. Am. Chem. Soc.,
2023, 145, 7621-7627.
Palladium/TY-Phos-Catalyzed Asymmetric Heck/Tsuji-Trost Reaction of o-Bromophenols
with 1,3-Dienes
Y. Tu, B. Xu, Q. Wang, H. Dong, Z.-M. Zhang, J. Zhang, J. Am. Chem. Soc.,
2023, 145, 4378-4383.
