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


More about the RSC Name Reaction Ontology (RXNO)

Articles referencing this term

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DOI: 10.1039/b803584a

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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
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DOI: 10.1039/b816812a

Simplified methods for the functionalisation of 3-hexoxythiophenes at the 5-position and further reactions to alkynyl and vinyl derivatives
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DOI: 10.1039/b817089d

Marriage of porphyrin chemistry with metal-catalysed reactions
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DOI: 10.1039/b817941g

Formation of pentacyclic structures by a domino sequence on cyclic enamides
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DOI: 10.1039/b820636h

Conjugated anthracene derivatives as donor materials for bulk heterojunction solar cells: olefinic versus acetylenic spacers
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DOI: 10.1039/b820829h

Recent advancements and challenges of palladiumII-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

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DOI: 10.1039/b903577j

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DOI: 10.1039/b904097h

Comparative catalytic C–H vs. C–Si activation of arenes with Pd complexes directed by urea or amide groups
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DOI: 10.1039/b905717j

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DOI: 10.1039/b908638b

Palladium(ii)-catalyzed coupling reactions with a chelating vinyl ether and arylboronic acids: a new Heck/Suzuki domino diarylation reaction
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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

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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
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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
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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