Heck reaction

Definition: A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. It is stereospecific.

ID: RXNO:0000024

Synonyms:

More about the RSC Name Reaction Ontology (RXNO)

Articles referencing this term

E factors, green chemistry and catalysis: an odyssey
Roger A. Sheldon, Chem. Commun., 2008 , 3352
DOI: 10.1039/b803584a

A versatile protocol for Stille–Migita cross coupling reactions
Alois Fürstner, Jacques-Alexis Funel, Martin Tremblay, Laure C. Bouchez, Cristina Nevado, Mario Waser, Jens Ackerstaff and Christopher C. Stimson, Chem. Commun., 2008 , 2873
DOI: 10.1039/b805299a

Anti-Markovnikov hydroarylation of styrenes catalyzed by an in situ generated ruthenium complex
Rémi Martinez, Jean-Pierre Genet and Sylvain Darses, Chem. Commun., 2008 , 3855
DOI: 10.1039/b806121a

Fused tetracycles with a benzene or cyclohexadiene core: [2 + 2 + 2] cycloadditions on macrocyclic systems
Sandra Brun, Lídia Garcia, Iván González, Anna Torrent, Anna Dachs, Anna Pla-Quintana, Teodor Parella and Anna Roglans, Chem. Commun., 2008 , 4339
DOI: 10.1039/b806524a

Palladium- (and nickel-) catalyzed vinylation of aryl halides
Scott E. Denmark and Christopher R. Butler, Chem. Commun., 2009 , 20
DOI: 10.1039/b809676g

Amino-sugar modular ligands—useful cores for the formation of asymmetric copper 1,4-addition catalysts
Antonella De Roma, Francesco Ruffo and Simon Woodward, Chem. Commun., 2008 , 5384
DOI: 10.1039/b813137f

Palladium-catalyzed decarboxylative coupling of aromatic acids with aryl halides or unactivated arenes using microwave heating
Adelina Voutchkova, Abigail Coplin, Nicholas E. Leadbeater and Robert H. Crabtree, Chem. Commun., 2008 , 6312
DOI: 10.1039/b813998a

The synthesis and applications of a micro-pine-structured nanocatalyst
Vivek Polshettiwar, Mallikarjuna N. Nadagouda and Rajender S. Varma, Chem. Commun., 2008 , 6318
DOI: 10.1039/b814715a

Diels–Alder cycloaddition as a new approach toward stable PC(sp ³ )P-metalated compounds
Clarite Azerraf, Alina Shpruhman and Dmitri Gelman, Chem. Commun., 2009 , 466
DOI: 10.1039/b815051f

Characterization of novel sulfonium photoacid generators and their microwave-assisted synthesis
Ciceron O. Yanez, Carolina D. Andrade and Kevin D. Belfield, Chem. Commun., 2009 , 827
DOI: 10.1039/b815831b

A thermal 6π electrocyclization strategy towards taiwaniaquinoids. First enantiospecific synthesis of (−)-taiwaniaquinone G
Enrique Alvarez-Manzaneda, Rachid Chahboun, Eduardo Cabrera, Esteban Alvarez, Ali Haidour, Jose Miguel Ramos, Ramón Alvarez-Manzaneda, Mohammed Hmamouchi and Hakima Es-Samti, Chem. Commun., 2009 , 592
DOI: 10.1039/b816812a

Simplified methods for the functionalisation of 3-hexoxythiophenes at the 5-position and further reactions to alkynyl and vinyl derivatives
Mike Joachim Zöllner, Ullrich Jahn, Eike Becker, Wolfgang Kowalsky and Hans-Hermann Johannes, Chem. Commun., 2009 , 565
DOI: 10.1039/b817089d

Marriage of porphyrin chemistry with metal-catalysed reactions
Hiroshi Shinokubo and Atsuhiro Osuka, Chem. Commun., 2009 , 1011
DOI: 10.1039/b817941g

Formation of pentacyclic structures by a domino sequence on cyclic enamides
Gedu Satyanarayana, Caecilia Maichle-Mössmer and Martin E. Maier, Chem. Commun., 2009 , 1571
DOI: 10.1039/b820636h

Conjugated anthracene derivatives as donor materials for bulk heterojunction solar cells: olefinic versus acetylenic spacers
Assunta Marrocchi, Fabio Silvestri, Mirko Seri, Antonio Facchetti, Aldo Taticchi and Tobin J. Marks, Chem. Commun., 2009 , 1380
DOI: 10.1039/b820829h

Recent advancements and challenges of palladium^II-catalyzed oxidation reactions with molecular oxygen as the sole oxidant
Keith M. Gligorich and Matthew S. Sigman, Chem. Commun., 2009 , 3854
DOI: 10.1039/b902868d

The first total synthesis of (±)-apparicine
M.-Lluïsa Bennasar, Ester Zulaica, Daniel Solé and Sandra Alonso, Chem. Commun., 2009 , 3372
DOI: 10.1039/b903577j

A critical look at reactions in class I and II gas-expanded liquids using CO₂ and other gases
Geoffrey R. Akien and Martyn Poliakoff, Green Chem., 2009 , 11 , 1083
DOI: 10.1039/b904097h

Comparative catalytic C–H vs. C–Si activation of arenes with Pd complexes directed by urea or amide groups
Waqar Rauf, Amber L. Thompson and John M. Brown, Chem. Commun., 2009 , 3874
DOI: 10.1039/b905717j

Coumarin-derivative-based off–on catalytic chemodosimeter for Cu²⁺ ions
Mi Hee Kim, Hyun Hye Jang, Sujung Yi, Suk-Kyu Chang and Min Su Han, Chem. Commun., 2009 , 4838
DOI: 10.1039/b908638b

Palladium(ii)-catalyzed coupling reactions with a chelating vinyl ether and arylboronic acids: a new Heck/Suzuki domino diarylation reaction
Alejandro Trejos, Ashkan Fardost, Samir Yahiaoui and Mats Larhed, Chem. Commun., 2009 , 7587
DOI: 10.1039/b918358b

Nanocontact-induced catalytic activation in palladium nanoparticles
Changlong Jiang, Sadananda Ranjit, Zhongyu Duan, Yu Lin Zhong, Kian Ping Loh, Chun Zhang and Xiaogang Liu, Nanoscale, 2009 , 1 , 391
DOI: 10.1039/b9nr00093c

Polymer brushes: Applications in biomaterials and nanotechnology
Neil Ayres, Polym. Chem., 2010 , 1 , 769
DOI: 10.1039/b9py00246d

A novel class of C _3d symmetrical molecules synthesized by a six-fold substitution from 1,4,5,8,9,12-hexabromododecahydrotriphenylene
Junfa Wei, Yanni Gao, Xiaoyan Ma, Xiaowei Jia, Xianying Shi and Zhanguo Chen, Chem. Commun., 2010 , 46 , 3738
DOI: 10.1039/c002680h

Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an intramolecular radical-oxidative cyclization of polysubstituted pyrroles, and evaluation of their cytotoxic activity
Paul E. Reyes-Gutiérrez, José R. Camacho, Ma. Teresa Ramírez-Apan, Yazmin M. Osornio and Roberto Martínez, Org. Biomol. Chem., 2010 , 8 , 4374
DOI: 10.1039/c004399k

Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
Chin Hui Kee, Azhar Ariffin, Khalijah Awang, Koichi Takeya, Hiroshi Morita, Salmaan Inayat Hussain, Kok Meng Chan, Pauline J. Wood, Michael D. Threadgill, Chuan Gee Lim, SeikWeng Ng, Jean Frédéric F. Weber and Noel F. Thomas, Org. Biomol. Chem., 2010 , 8 , 5646
DOI: 10.1039/c0ob00296h

Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules
Henrik Sundén and Roger Olsson, Org. Biomol. Chem., 2010 , 8 , 4831
DOI: 10.1039/c0ob00331j

Reusable polystyrene-supported Pd catalyst for Mizoroki–Heck reactions with extremely low amounts of supported Pd
Carine Diebold, Stéphane Schweizer, Jean-Michel Becht and Claude Le Drian, Org. Biomol. Chem., 2010 , 8 , 4834
DOI: 10.1039/c0ob00523a

The organocatalytic three-step total synthesis of (+)-frondosin B
Maud Reiter, Staffan Torssell, Sandra Lee and David W. C. MacMillan, Chem. Sci., 2010 , 1 , 37
DOI: 10.1039/c0sc00204f