Online citations, reference lists, and bibliographies.
← Back to Search

Low Pressure Vinylation Of Aryl And Vinyl Halides Via Heck-Mizoroki Reactions Using Ethylene.

Craig R. Smith, T. V. RajanBabu
Published 2010 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy Visualize in Litmaps
Share
Reduce the time it takes to create your bibliography by a factor of 10 by using the world’s favourite reference manager
Time to take this seriously.
Get Citationsy
Aryl bromides and iodides in the presence of catalytic amounts of a palladacycle derived from acetophenone oxime and 2 equivalents of potassium acetate react with ethylene under ambient pressure (15-30 psi) to give the corresponding vinylarenes. The reactions work with both electron-deficient and electron-rich aryl compounds and tolerate wide variety of common functional groups. Vinyl bromides lead to 1,3-dienes in moderate yields.
This paper references
Chem. Soc. J. Org. Chem. Eur. J. Org. Chem. Eur. J. Org. Chem. Tetrahedron Lett. J. Organomet. Chem. Synlett Org. Lett. J. Org. Chem. Tetrahedron Lett
D S J Matteson (1075)
J. Am. Chem. Soc. Org. Lett. J. Org. Chem. Synthesis J. Org. Chem
A F Littke (1170)
J. Chem. Soc., Chem. Commun
P E Riley (1287)
Synthesis Tetrahedron Lett. Org. Lett
D A Alonso (1451)
For a compilation of references that deal with the possible mechanism of the reaction under these conditions, see Ref. 10b. 22
C R Smith (1511)
Clear liquid. References and notes 1 In Transition Metals for Organic Synthesis
R F Heck (1553)
O O ARTICLE IN PRESS Please cite this article in press as: Smith
J Dupont (1715)
A recent review of palladacycles
A J Spencer (1844)
10.1002/JLAC.18510780302
Beiträge zur Kenntniss der flüchtigen organischen Basen
A. W. Hofmann (1850)
Org. React. Jr. J. Am. Chem. Soc
A W Hofmann (1851)
10.1021/JA01501A029
Radical-catalyzed Additions to α,β-Unsaturated Boronic Esters1,2
D. S. Matteson (1960)
10.1021/JA01022A034
Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivatives
R. Heck (1968)
10.1246/BCSJ.43.3480
Aromatic Metalation Reactions by Palladium(II) and Platinum(II) on Aromatic Aldoximes and Ketoximes
H. Onoue (1970)
Adv. Synth. Catal. Bull. Chem. Soc. Jpn. J. Organomet. Chem. Dalton Trans. Can. J. Chem. J. Chem. Soc., Chem. Commun. J. Org. Chem
D A Alonso (1970)
10.1021/JA00749A080
Asymmetric homogeneous hydrosilylation with platinum(II) complexes of chiral phosphines
K. Yamamoto (1971)
10.1246/BCSJ.44.581
Arylation of Olefin with Aryl Iodide Catalyzed by Palladium
T. Mizoroki (1971)
10.1039/C39720001287
Three-co-ordinate cobalt(II). The crystal structure of fully-dehydrated partially-CoII-exchanged zeolite A
P. Riley (1972)
10.1021/jo00001a600
For a recent review
(1973)
10.1039/C39750000687
Six-membered ortho-metallated ring systems
N. Cameron (1975)
10.1246/BCSJ.49.1958
Nickel-Phosphine Complex-Catalyzed Grignard Coupling. I. Cross-Coupling of Alkyl, Aryl, and Alkenyl Grignard Reagents with Aryl and Alkenyl Halides: General Scope and Limitations
K. Tamao (1976)
10.1021/JO00406A033
Palladium-catalyzed arylation of ethylene
J. E. Plevyak (1978)
10.1021/JO00408A041
Rapid chromatographic technique for preparative separations with moderate resolution
W. C. Still (1978)
J. Org. Chem
W C Still (1978)
For a recent report on the use of ligand-free Pd salts, see: (b) de Vries
A Luzikova (1978)
Tetrahedron Chem. Soc. J. Am. Chem. Soc. J. Am. Chem. Soc
R H Grubbs (1980)
10.1021/jo00335a019
Ortho vinylation of aromatic amides via cyclopalladation complexes
H. Horino (1981)
10.1016/0022-328X(83)89511-4
A highly efficient version of the palladium-catalysed arylation of alkenes with aryl bromides
A. Spencer (1983)
10.1021/JA00336A045
Mechanisms of elimination reactions. 38. Why is the effect of successive .beta.-alkyl substitution on the rates of elimination from quaternary ammonium salts nonadditive?
Shune‐Long Wu (1984)
Org React 1953;7:99
AW Hofmann (1984)
10.1021/JO00225A072
Nickel-catalyzed Markovnikov addition of hydrogen cyanide to olefins. Application to nonsteroidal antiinflammatories
W. A. Nugent (1985)
10.1016/S0040-4039(00)96649-8
Hydrozirconation methods for natural isobutylamides (anacyclin, pellitorine and its vinylogue) and synthons.
L. Crombie (1987)
10.1021/JA00252A029
Palladium-catalyzed coupling of aryl triflates with organostannanes
A. Echavarren (1987)
10.1021/JO00379A020
Synthesis of functionalized styrenes via palladium-catalyzed coupling of aryl bromides with vinyl tin reagents
D. R. Mckean (1987)
10.1021/JA00257A036
Asymmetric hydroformylation catalyzed by homogeneous and polymer-supported platinum complexes containing chiral phosphine ligands
G. Parrinello (1987)
10.1021/JO00239A056
Cross-coupling of organosilanes with organic halides mediated by a palladium catalyst and tris(diethylamino)sulfonium difluorotrimethylsilicate
Y. Hatanaka (1988)
10.1021/JO00241A010
Palladium-catalyzed coupling of 2-bromoanilines with vinylstannanes. A regiocontrolled synthesis of substituted indoles
M. E. Krolski (1988)
Synthesis 1998:1544
AF Littke (1988)
Synthesis 2000:999
SE Denmark (1988)
Org. Lett. Synthesis Z. J. Organomet. Chem. J. Org. Chem
S E Denmark (1988)
10.1039/DT9890001715
Reactions of cyclopalladated compounds. Part 21. Various examples of sulphur-assisted intramolecular palladation of aryl and alkyl groups
J. Dupont (1989)
10.1021/JA00163A052
Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by (salen)Manganese Complexes
Wei Zhang (1990)
10.1039/P19910001511
Syntheses of the ethyl esters of the plant host-selective (H-S) toxins (AF-IIa, AF-IIc and AK-II) produced by pathotypes of Alternaria alternata
L. Crombie (1991)
Tetrahedron Lett 1987;28:4875
L Crombie (1991)
10.1016/0040-4039(94)80027-8
Catalytic asymmetric hydrosilylation of conjugated dienes: Effective control of regio- and enantioselectivities
Y. Hatanaka (1994)
10.1016/0022-328X(94)88213-4
Synthesis of trans-arylvinylboronates via a palladium catalysed cross-coupling of a vinylboronate ester with aryl halides
S. Stewart (1994)
10.1021/JA00101A007
Ligand Electronic Effects in Asymmetric Catalysis - Enhanced Enantioselectivity in the Asymmetric Hydrocyanation of Vinylarenes
A. Casalnuovo (1994)
10.1002/ANIE.199518441
Palladacycles as Structurally Defined Catalysts for the Heck Olefination of Chloro- and Bromoarenes†‡
W. Herrmann (1995)
10.1021/JA9609112
Role of Electronic Asymmetry in the Design of New Ligands: The Asymmetric Hydrocyanation Reaction
T. V. RajanBabu (1996)
10.1021/OM970064R
THE TRANS-CHLOROPALLADATION REACTION OF PROPARGYL AMINES AND THIOETHERS. X-RAY CRYSTAL STRUCTURE OF TRANS-PD-TRANS-C(PH)=C(CL)CH(ME)S(I-PR)(CL)(PY)
J. Dupont (1997)
10.1016/S0022-328X(96)06794-0
Palladium catalyzed cross-coupling reaction of Grignard reagents with halobenzoic acids, halophenols and haloanilines
N. A. Bumagin (1997)
10.1021/JA973548N
The Hydrovinylation Reaction: A New Highly Selective Protocol Amenable to Asymmetric Catalysis
N. Nomura (1998)
10.1016/S0040-4039(98)02175-3
ORTHOPALLADATED TRIARYLPHOSPHITE COMPLEXES AS HIGHLY EFFICIENT CATALYSTS IN THE HECK REACTION
David A. Albisson (1998)
10.1016/S0040-4039(98)01003-X
POTASSIUM VINYLTRIFLUOROBORATE : A STABLE AND EFFICIENT VINYLATING AGENT OF ARENEDIAZONIUM SALTS USING PALLADIUM CATALYSTS
Sylvain Darses (1998)
10.1039/A802642D
Highly active, stable, catalysts for the Heck reaction; further suggestions on the mechanism
B. Shaw (1998)
10.1055/S-1998-2172
CROSS-COUPLING REACTION OF ORGANOSTANNANES WITH ARYL HALIDES CATALYZED BY NICKEL- TRIPHENYLPHOSPHINE OR NICKEL-LITHIUM HALIDE COMPLEX
E. Shirakawa (1998)
10.1002/9783527619399
Transition Metals for Organic Synthesis
M. Beller (1998)
Chem Commun 1998:1361
BL Shaw (1998)
10.1002/(SICI)1099-0690(199908)1999:8<1875::AID-EJOC1875>3.0.CO;2-W
Potassium Organotrifluoroborates: New Partners in Palladium‐Catalysed Cross‐Coupling Reactions
Sylvain Darses (1999)
10.1016/S0022-328X(98)01050-X
Application of palladacycles in Heck type reactions
W. Herrmann (1999)
10.1055/S-2000-6292
1-Methyl-1-vinyl- and 1-Methyl-1-(prop-2-enyl)silacyclobutane: Reagents for Palladium-Catalyzed Cross-Coupling Reactions of Aryl Halides
S. Denmark (2000)
10.1021/CR9903048
The heck reaction as a sharpening stone of palladium catalysis.
I. Beletskaya (2000)
10.1021/OL0058644
Oxime Palladacycles: Stable and Efficient Catalysts for Carbon-Carbon Coupling Reactions.
Alonso (2000)
10.1016/S0022-328X(00)00894-9
Cross-coupling of vinylpolysiloxanes with aryl iodides
S. Denmark (2001)
10.1021/OL006827F
Palladium/imidazolium salt catalyzed coupling of aryl halides with hypervalent organostannates.
G. Grasa (2001)
10.1016/S0022-328X(00)00876-7
NC-palladacycles as highly effective cheap precursors for the phosphine-free Heck reactions
I. Beletskaya (2001)
10.1021/JA020012F
Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.
A. Littke (2002)
10.1021/JO025619T
Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions.
D. Alonso (2002)
10.1021/OL0169729
Suzuki cross-coupling reactions of potassium alkenyltrifluoroborates.
Gary A. Molander and (2002)
10.1002/1521-3773(20020104)41:1<179::AID-ANIE179>3.0.CO;2-O
A convenient oxime-carbapalladacycle-catalyzed Suzuki cross-coupling of aryl chlorides in water.
L. Botella (2002)
10.1002/1615-4169(200202)344:2<172::AID-ADSC172>3.0.CO;2-9
Oxime-Derived Palladium Complexes as Very Efficient Catalysts for the Heck–Mizoroki Reaction
D. Alonso (2002)
10.1016/S0022-328X(02)01727-8
Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles
L. Botella (2002)
10.1021/JO020074O
Generation of substituted styrenes via Suzuki cross-coupling of aryl halides with 2,4,6-trivinylcyclotriboroxane.
Fergal Kerins (2002)
J. Org. Chem
C Pacheco (2002)
Chem Ná Jera (2002)
10.1021/OL0341849
Di-2-pyridylmethylamine-based palladium complexes as new catalysts for Heck, Suzuki, and Sonogashira reactions in organic and aqueous solvents.
C. Nájera (2003)
10.1021/JA0375535
Intermolecular, markovnikov hydroamination of vinylarenes with alkylamines.
M. Utsunomiya (2003)
10.1021/OL035184B
Homeopathic ligand-free palladium as a catalyst in the heck reaction. A comparison with a palladacycle.
A. D. de Vries (2003)
10.1039/B304053D
Phosphine and arsine adducts of N-donor palladacycles as catalysts in the Suzuki coupling of aryl bromides
R. Bedford (2003)
Org Chem 1978;43:2454.For a recent report on the use of ligand-free Pd-salts
JE Plevyak (2003)
10.1002/EJOC.200300627
Suzuki Cross‐Coupling Reactions between Alkenylboronic Acids and Aryl Bromides Catalysed by a Tetraphosphane‐Palladium Catalyst
Eugénie Peyroux (2004)
10.1002/ADSC.200404178
High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview
V. Farina (2004)
10.1002/9783527619535
Metal-catalyzed cross-coupling reactions
A. D. Meijere (2004)
10.1016/J.TETLET.2004.01.024
Controlled mono and double Heck reactions in water catalyzed by an oxime-derived palladacycle
L. Botella (2004)
10.1021/CR030681R
The potential of palladacycles: more than just precatalysts.
J. Dupont (2005)
10.1139/V05-109
In vitro and in vivo studies of neutral cyclometallated complexes against murine leukæmias
G. L. Edwards (2005)
10.1021/JA0561338
Hydrovinylation of 1,3-dienes: a new protocol, an asymmetric variation, and a potential solution to the exocyclic side chain stereochemistry problem.
Aibin Zhang (2006)
10.1021/JA060999B
All-Carbon Quaternary Centers via Catalytic Asymmetric Hydrovinylation. New Approaches to the Exocyclic Side Chain Stereochemistry Problem
Aibin Zhang (2006)
10.1021/OL052517R
Vinylation of aryl bromides using an inexpensive vinylpolysiloxane.
S. Denmark (2006)
10.1021/JO0617013
Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles.
G. Molander (2006)
10.1021/JO061346G
A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents.
Alberto Spaggiari (2007)
10.1021/cr0306788
Hydroamination: direct addition of amines to alkenes and alkynes.
T. Müller (2008)
10.1021/ol800395m
Efficient, selective, and green: catalyst tuning for highly enantioselective reactions of ethylene.
C. R. Smith (2008)
10.1021/ol802024j
First cross-coupling reaction of potassium aryltrifluoroborates with organic chlorides in aqueous media catalyzed by an oxime-derived palladacycle.
E. Alacid (2008)
10.1016/J.TETLET.2008.05.119
Efficient heterogeneous vinylation of aryl halides using potassium vinyltrifluoroborate
Lionel Joucla (2008)
10.1016/J.TETLET.2008.05.017
Expedient synthesis and solvent dependent oxidation behavior of a water-soluble IBX derivative
Amitha Kommreddy (2008)
Organomet Chem 2002;663:46
DA Alonso (2008)
Tetrahedron Lett 1998;39:5045
DS Matteson (2008)
10.1021/jo900198b
Catalytic asymmetric synthesis using feedstocks: an enantioselective route to 2-arylpropionic acids and 1-arylethyl amines via hydrovinylation of vinyl arenes.
C. R. Smith (2009)
10.1016/J.JORGANCHEM.2008.11.065
NC palladacycles in the heck arylation of ethylene: synthesis, structure and their reactivity
Shashi B. Atla (2009)
10.1055/S-0028-1088213
In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.
T. V. RajanBabu (2009)
Tetrahedron
Article Smith (2009)
C; retention time (min): 12.44



This paper is referenced by
10.3390/molecules25153421
Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids
H. Neumann (2020)
10.1021/acs.joc.0c01173
Iron-Catalyzed Direct Julia-type Olefination of Alcohols.
V. G. Landge (2020)
10.1002/chem.201902022
Pd-Catalyzed Synthesis of Vinyl Arenes from Aryl Halides and Acrylic Acid.
Yang Gao (2019)
10.1002/ADSC.201900365
Synthesis and Catalytic Applications of [N,N]‐Pyrrole Ligands for the Regioselective Synthesis of Styrene Derivatives
F. Hochberger‐Roa (2019)
10.1021/acsomega.9b02191
Ligand-Promoted Iridium-Catalyzed Transfer Hydrogenation of Terminal Alkynes with Ethanol and Its Application
Chengniu Wang (2019)
10.1002/CJOC.201800354
Rhodium(III)‐Catalyzed C—H Vinylation of Arenes: Access to Functionalized Styrenes
Jun Zhou (2018)
10.1002/ADSC.201800167
Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene
H. Barlow (2018)
10.1055/S-0036-1589095
Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400
Felipe C. Demidoff (2017)
10.1021/ACS.OPRD.6B00362
Development and Scaling-Up of the Fragrance Compound 4-Ethylguaiacol Synthesis via a Two-Step Chemo-Enzymatic Reaction Sequence
Lorenzo Pesci (2017)
10.1002/cctc.201600035
Oxime‐Derived Palladacycles: Applications in Catalysis
C. Nájera (2016)
10.1126/science.aaf7783
Enantioselective cyanation of benzylic C–H bonds via copper-catalyzed radical relay
Wen-wu Zhang (2016)
10.1016/J.PORGCOAT.2015.02.006
Aldehyde functional monomer as efficient cross-linkable comonomer with biobased phenols in acrylic coatings
Gabriel Foyer (2015)
10.1016/B978-0-08-097742-3.00533-4
5.32 Hydrovinylation Reactions in Organic Synthesis
T. V. RajanBabu (2014)
10.1021/OM500319H
Iron-Catalyzed Hydromagnesiation: Synthesis and Characterization of Benzylic Grignard Reagent Intermediate and Application in the Synthesis of Ibuprofen
M. Greenhalgh (2014)
10.1002/anie.201303916
Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.
Vaneet Saini (2013)
10.1002/ANGE.201303916
Übergangsmetallkatalysierte C‐C‐Kupplungen mit Ethylen im Labormaßstab
Vaneet Saini (2013)
10.1002/cctc.201200778
Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes
Samuel L. Bourne (2013)
10.1021/ja201321v
Ethylene in organic synthesis. Repetitive hydrovinylation of alkenes for highly enantioselective syntheses of pseudopterosins.
Daniel J. Mans (2011)
10.1021/ja103834b
Rh catalyzed olefination and vinylation of unactivated acetanilides.
F. Patureau (2010)
10.1002/CHIN.201023056
Low Pressure Vinylation of Aryl and Vinyl Halides via Heck—Mizoroki Reactions Using Ethylene.
C. R. Smith (2010)
Semantic Scholar Logo Some data provided by SemanticScholar