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The Palladium‐Catalyzed Cross‐Coupling Reactions Of Organotin Reagents With Organic Electrophiles [New Synthetic Methods (58)]

J. Stille
Published 1986 · Chemistry

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The cross-coupling of organotin reagents with a variety of organic electrophiles, catalyzed by palladium, provides a novel method for generating a carbon-carbon bond. Because this mild, versatile reaction is tolerant of a wide variety of functional groups on either coupling partner, is stereospecific and regioselective, and gives high yields of product, it is ideal for use in the synthesis of elaborate organic molecules. When the coupling reaction is carried out in the presence of carbon monoxide, instead of a direct coupling, carbon monoxide insertion takes place, stitching the two coupling partners together and generating a ketone.



This paper is referenced by
10.1246/CL.1990.185
A First Palladium-Catalyzed Aryldegermylation of Styryltrimethylgermanes
K. Ikenaga (1990)
10.1002/JHET.5570280621
Synthesis of 7-(alkenyl, cycloalkenyl, and 1,2,3,6-tetrahydro-4-pyridinyl)quinolones
J. Kiely (1991)
10.1016/0923-1137(93)90093-U
Tin for organic synthesis, part 9
W. P. Neumann (1993)
10.1016/S0040-4039(00)93384-7
Convergent approaches to the Vitamin D skeleton using a transition metal catalyzed carbometalation/capture strategy
J. M. Nuss (1993)
10.1016/S0040-4020(01)85633-7
Synthetic studies on dynemicin A. New quinoline synthesis for C, D and E rings.
T. Nishikawa (1994)
10.1016/0040-4020(96)00617-5
A new stereoselective synthesis of chiral γ-functionalized (E)-allylic amines
G. Reginato (1996)
10.1016/0020-1693(95)04869-3
Synthesis of (porphinato)zinc(II)-spacer-(porphinato)iron(III) chloride complexes: a modular approach to fixed-distance electron-transfer model compounds through the efficacy of metal-mediated cross-coupling
P. J. D. Rege (1996)
10.1016/0040-4039(96)00970-7
A new route to 2-substituted Δ2-thiazolines: Stille cross-couplings of 2-bromo-Δ2-thiazolines
W. D. Schmitz (1996)
10.1039/A704108J
Rhodium-catalysed arylation of aldehydes with arylstannanes
S. Ōi (1997)
10.1016/S1381-1177(97)00007-6
Synthesis of chiral building blocks for organic synthesis via lipase-catalyzed reaction: New method of enhancing enzymatic reaction enantioselectivity
T. Itoh (1997)
10.1016/S0040-4039(97)10278-7
THE SYNTHESIS OF GABAA ACTIVE LIGANDS BY THE STILLE PROCESS
T. Gan (1997)
10.1039/B008811K
Snapshots of a Stille reaction
A. Casado (2001)
10.1002/1521-3757(20010601)113:11<2125::AID-ANGE2125>3.0.CO;2-1
Synthese von Apoptolidinon
Julia Schuppan (2001)
10.1016/S0040-4039(01)02193-1
Palladium-catalyzed coupling of aryl halides with arylhalosilanes in air and water
T. Huang (2002)
10.1002/1521-3757(20011217)113:24<4676::AID-ANGE4676>3.0.CO;2-B
DieB-Alkyl-Suzuki-Miyaura-Kreuzkupplung: Entwicklung, Untersuchungen zum Mechanismus und Anwendungen in der Naturstoffsynthese
S. Chemler (2001)
10.1039/b205765d
The direct use of phenyldimethylsilanes in silicon assisted palladium catalysed cross coupling.
J. C. Anderson (2002)
10.1021/OL060162L
Synthesis of homopolymer containing diphenyl end-capped oligothiophene co-oligomer unit in the side chain.
Chunchang Zhao (2006)
Synthèse et évaluation pharmacologique d'imidazolidin-2-ones et d'analogues à potentialités immunosuppressives
Caroline Denevault (2007)
10.1039/B513587G
Palladium-coated nickel nanoclusters: new Hiyama cross-coupling catalysts.
L. Durán Pachón (2006)
10.1002/PRAC.19983400114
PD2(DBA)3 . CHCL3/ASPH3 : A POWERFUL CATALYST SYSTEM FOR PD(0)-MEDIATED C-C-BOND FORMATION
R. Faust (1998)
10.1016/S0040-4039(98)00170-1
Enantioselective synthesis of α-hydroxy thioesters via oxazaborolidine-mediated reduction of α-phenylthio enones
R. Berenguer (1998)
10.1271/bbb.63.1253
Synthesis of the Methyl Ester of Tritium-labeled AK-toxin I, a Host-specific Toxin Produced by Alternaria alternata Japanese Pear Pathotype.
M. Okada (1999)
10.1016/S0040-4039(99)00575-4
Stereospecific stille-coupling reaction of (Z)-1,2-bis(trimethylstannyll)ethenes with hypervalent iodonium salts
S. Kang (1999)
10.1016/S0040-4020(99)00184-2
Reaction of acyl chlorides with organometallic reagents: A banquet table of metals for ketone synthesis
R. Dieter (1999)
10.1016/S0040-4039(99)01236-8
A practical iodination of aromatic compounds using tetrabutylammonium peroxydisulfate and iodine
S. G. Yang (1999)
10.1002/(SICI)1521-3757(19991018)111:20<3201::AID-ANGE3201>3.0.CO;2-Z
AUF DEM WEG ZU WIRKSAMEN UND VIELSEITIGEN METALL-KATALYSIERTEN ALKYL-ALKYL-KREUZKUPPLUNGEN
D. Cárdenas (1999)
10.1021/OL000128L
Asymmetric total synthesis of (-)-mycothiazole.
Hiroshi Sugiyama (2000)
10.1021/OL005508L
Formation of homoallyl stannanes via palladium-catalyzed stannylative cyclization of enynes
Lautens (2000)
10.1016/J.POLYMER.2007.07.051
Synthesis of π-conjugated polymers bearing electronic and optical functionalities by organometallic polycondensations and their chemical properties
T. Yamamoto (2007)
10.1080/00397910701545171
Facile Synthesis of E‐Diiodoalkenes: H2O2‐Activated Reaction of Alkynes with Iodine
A. Terent’ev (2007)
10.1016/J.TETLET.2007.08.025
Regioselective cross-coupling of allylindium reagents with activated benzylic bromides - a simple and efficient procedure for the synthesis of terminal alkenes
B. Ranu (2007)
10.1002/chem.200800558
Stannylated polynorbornenes as new reagents for a clean Stille reaction.
Nora Carrera (2008)
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