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Equation Name Summary Source
2-(4-METHOXYPHENYL)-2-CYCLOHEXEN-1-ONE: PREPARATION OF 2-IODO-2-CYCLOHEXEN-1-ONE AND SUZUKI COUPLING WITH 4-METHOXYPHENYLBORONIC ACID (2-Cyclohexen-1-one, 2-(4-methoxyphenyl)- and 2-Cyclohexen-1-one, 2-iodo-)) Cross-coupling Preparation of 2-Cyclohexen-1-one, 2-(4-methoxyphenyl)- and 2-Cyclohexen-1-one, 2-iodo-). Submitted by Frederic S. Ruel, Matthew P. Braun, and Carl R. Johnson1. DOI: 10.15227/orgsyn.075.0069. Organic Syntheses
ACCELERATED SUZUKI COUPLING VIA A LIGANDLESS PALLADIUM CATALYST: 4-METHOXY-2'-METHYLBIPHENYL (1,1'-Biphenyl, 4'-methoxy-2-methyl-) Cross-coupling Preparation of 1,1'-Biphenyl, 4'-methoxy-2-methyl-. Submitted by Felix E. Goodson, Thomas I. Wallow1 , and Bruce M. Novak2. DOI: 10.15227/orgsyn.075.0061. Organic Syntheses
ALKYNYL(PHENYL)IODONIUM TOSYLATES: PREPARATION AND STEREOSPECIFIC COUPLING WITH VINYLCOPPER REAGENTS. FORMATION OF CONJUGATED ENYNES. 1-HEXYNYL(PHENYL)IODONIUM TOSYLATE AND (E)-5-PHENYLDODEC-5-EN-7-YNE (Iodine, 1-hexynyl(4-methylbenzenesulfonato-O)phenyl- and Benzene, (1-butyl-1-octen-3-ynyl)-, (E)-) Cross-coupling Preparation of Iodine, 1-hexynyl(4-methylbenzenesulfonato-O)phenyl- and Benzene, (1-butyl-1-octen-3-ynyl)-, (E)-. Submitted by Peter J. Stang and Tsugio Kitamura1. DOI: 10.15227/orgsyn.070.0215. Organic Syntheses
B-PROTECTED HALOBORONIC ACIDS FOR ITERATIVE CROSS-COUPLING Cross-coupling Preparation of B-PROTECTED HALOBORONIC ACIDS FOR ITERATIVE CROSS-COUPLING. Submitted by Steven G. Ballmer, Eric P. Gillis, and Martin D. Burke1. DOI: 10.15227/orgsyn.086.0344. Organic Syntheses
Buchwald–Hartwig amination Cross-coupling In organic chemistry, the Buchwald–Hartwig amination is a chemical reaction for the synthesis of carbon–nitrogen bonds via the palladium-catalyzed coupling reactions of amines with aryl halides. Altho… Wikipedia: Category:Name reactions
Cadiot–Chodkiewicz coupling Cross-coupling The Cadiot–Chodkiewicz coupling in organic chemistry is a coupling reaction between a terminal alkyne and a haloalkyne catalyzed by a copper(I) salt such as copper(I) bromide and an amine base. The re… Wikipedia: Category:Name reactions
Castro–Stephens coupling Cross-coupling The Castro–Stephens coupling is a cross coupling reaction between a copper(I) acetylide and an aryl halide in pyridine, forming a disubstituted alkyne and a copper(I) halide. Wikipedia: Category:Name reactions
Chan–Lam coupling Cross-coupling The Chan–Lam coupling reaction, also known as the Chan–Evans–Lam coupling, is a cross-coupling reaction between an aryl boronic acid and an alcohol or an amine to form the corresponding secondary aryl… Wikipedia: Category:Name reactions
COUPLING OF o-TOLIDINE AND CHICAGO ACID (Preparation of a Salt-Free Azo Dye) Cross-coupling Preparation of Preparation of a Salt-Free Azo Dye. Submitted by J. L. Hartwell and Louis F. Fieser. DOI: 10.15227/orgsyn.016.0012. Organic Syntheses
Discussion addendum for: 4-METHOXY-4'-NITROPHENYL. RECENT ADVANCES IN THE STILLE BIARYL COUPLING REACTION AND APPLICATIONS IN COMPLEX NATURAL PRODUCTS SYNTHESIS Cross-coupling Preparation of Discussion addendum for: 4-METHOXY-4'-NITROPHENYL. RECENT ADVANCES IN THE STILLE BIARYL COUPLING REACTION AND APPLICATIONS IN COMPLEX NATURAL PRODUCTS SYNTHESIS. Submitted by Robert M. … Organic Syntheses
Discussion Addendum for: PALLADIUM CATALYZED CROSS-COUPLING OF (Z)-1-HEPTENYLDIMETHYLSILANOL WITH 4-IODOANISOLE: (Z)-(1-HEPTENYL)-4-METHOXYBENZENE Cross-coupling Preparation of Discussion Addendum for: PALLADIUM CATALYZED CROSS-COUPLING OF (Z)-1-HEPTENYLDIMETHYLSILANOL WITH 4-IODOANISOLE: (Z)-(1-HEPTENYL)-4-METHOXYBENZENE. Submitted by Scott E. Denmark * and J… Organic Syntheses
Discussion Addendum for: Suzuki-Miyaura Cross-Coupling: Preparation of 2'-Vinylacetanilide Cross-coupling Preparation of Discussion Addendum for: Suzuki-Miyaura Cross-Coupling: Preparation of 2'-Vinylacetanilide. Submitted by Donal F. O'Shea.*1. DOI: 10.15227/orgsyn.089.0202. Organic Syntheses
Discussion Addendum for: Synthesis of 4-, 5-, and 6-Methyl-2,2'-Bipyridine by a Negishi Cross-Coupling Strategy: 5-Methyl-2,2'-Bipyridine Cross-coupling Preparation of Discussion Addendum for: Synthesis of 4-, 5-, and 6-Methyl-2,2'-Bipyridine by a Negishi Cross-Coupling Strategy: 5-Methyl-2,2'-Bipyridine. Submitted by Tiandong Liu and Cassandra L. Fra… Organic Syntheses
Fukuyama coupling Cross-coupling The Fukuyama coupling is a coupling reaction taking place between a thioester and an organozinc halide in the presence of a palladium catalyst. The reaction product is a ketone. This reaction was disc… Wikipedia: Category:Name reactions
Glaser coupling Cross-coupling The Glaser coupling is a type of coupling reaction. It is by far one of the oldest coupling reactions and is based on copper compounds like copper(I) chloride or copper(I) bromide and an additional ox… Wikipedia: Category:Name reactions
Heck–Matsuda reaction Cross-coupling The Heck–Matsuda (HM) reaction is an organic reaction and a type of palladium catalysed arylation of olefins that uses arenediazonium salts as an alternative to aryl halides and triflates. Wikipedia: Category:Name reactions
Heck reaction Cross-coupling The Heck reaction (also called the Mizoroki–Heck reaction) is the chemical reaction of an unsaturated halide (or triflate) with an alkene in the presence of a base and a palladium catalyst to form a … Wikipedia: Category:Name reactions
HECK REACTIONS OF ARYL CHLORIDES CATALYZED BY PALLADIUM/TRI-tert-BUTYLPHOSPHINE: (E)-2-METHYL-3-PHENYLACRYLIC ACID BUTYL ESTER AND (E)-4-(2-PHENYLETHENYL)BENZONITRILE (2-Propenoic acid, 2-methyl-3-phenyl-, butyl ester and Benzonitrile, 4-[(1E)-2-phenylethenyl]) Cross-coupling Preparation of 2-Propenoic acid, 2-methyl-3-phenyl-, butyl ester and Benzonitrile, 4-[(1E)-2-phenylethenyl]. Submitted by Adam F. Littke and Gregory C. Fu1. DOI: 10.15227/orgsyn.081.0063. Organic Syntheses
Hirao coupling Cross-coupling In organic chemistry, Hirao coupling is a chemical reaction for the formation of carbon-phosphorus bonds using palladium cross-coupling. Hirao coupling expands the scope of carbon-phosphorus bond form… Wikipedia: Category:Name reactions
Hiyama coupling Cross-coupling The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds (C-C bonds). This reaction was discover… Wikipedia: Category:Name reactions
INTRAMOLECULAR OXIDATIVE COUPLING OF A BISENOLATE: 4-METHYLTRICYCLO[2.2.2.03,5]OCTANE-2,6-DIONE (Tricyclo[3.2.1.02,7]octane-6,8-dione, 2-methyl-) Cross-coupling Preparation of Tricyclo[3.2.1.02,7]octane-6,8-dione, 2-methyl-. Submitted by Marc-André Poupart, Gilbert Lassalle, and Leo A. Paquette1. DOI: 10.15227/orgsyn.069.0173. Organic Syntheses
Kumada coupling Cross-coupling In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard reagent and an organic halide. The procedure use… Wikipedia: Category:Name reactions
Liebeskind–Srogl coupling Cross-coupling The Liebeskind–Srogl coupling reaction is an organic reaction forming a new carbon–carbon bond from a thioester and a boronic acid using a metal catalyst. It is a cross-coupling reaction. This reactio… Wikipedia: Category:Name reactions
Murahashi coupling Cross-coupling The Murahashi Coupling is a cross coupling reaction. The coupling partners are organolithiums and organic halides. Transition metal catalysts are required. The reaction was first reported by Shun-Ich… Wikipedia: Category:Name reactions
Negishi coupling Cross-coupling The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon–carbon bonds … Wikipedia: Category:Name reactions
NICKEL-CATALYZED ASYMMETRIC NEGISHI CROSS-COUPLINGS OF RACEMIC SECONDARY ALLYLIC CHLORIDES WITH ALKYLZINCS: (S,E)-ETHYL 6-(1,3-DIOXOLAN-2-YL)-4-METHYLHEX-2-ENOATE (2-Hexenoic acid, 6-(1,3-dioxolan-2-yl)-4-methyl-, ethyl ester, (2E,4S)-) Cross-coupling Preparation of 2-Hexenoic acid, 6-(1,3-dioxolan-2-yl)-4-methyl-, ethyl ester, (2E,4S)-. Submitted by Sha Lou and Gregory C. Fu1. DOI: 10.15227/orgsyn.087.0317. Organic Syntheses
Nickel-Catalyzed Cross-Coupling of Aryl Halides with Alkyl Halides: Ethyl 4-(4-(4-methylphenylsulfonamido)-phenyl)butanoate Cross-coupling Preparation of Nickel-Catalyzed Cross-Coupling of Aryl Halides with Alkyl Halides: Ethyl 4-(4-(4-methylphenylsulfonamido)-phenyl)butanoate. Submitted by Daniel A.Everson, David T.George, and Daniel J.… Organic Syntheses
NICKEL-CATALYZED ENANTIOSELECTIVE NEGISHI CROSS-COUPLINGS OF RACEMIC SECONDARY α-BROMO AMIDES WITH ALKYLZINC REAGENTS: (S)-N-BENZYL-7-CYANO-2-ETHYL-N-PHENYLHEPTANAMIDE (Heptanamide, 7-cyano-2-ethyl-N-phenyl-N-(phenylmethyl)-, (2S)-) Cross-coupling Preparation of Heptanamide, 7-cyano-2-ethyl-N-phenyl-N-(phenylmethyl)-, (2S)-. Submitted by Sha Lou and Gregory C. Fu1. DOI: 10.15227/orgsyn.087.0330. Organic Syntheses
ONE-POT DIAZOTIZATION AND HECK REACTION OF METHYL ANTHRANILATE: 2-(3-OXOPROPYL)BENZOIC ACID METHYL ESTER Cross-coupling Preparation of ONE-POT DIAZOTIZATION AND HECK REACTION OF METHYL ANTHRANILATE: 2-(3-OXOPROPYL)BENZOIC ACID METHYL ESTER. Submitted by Florencio Zaragoza1. DOI: 10.15227/orgsyn.087.0226. Organic Syntheses
PALLADIUM-CATALYZED ALKYL-ALKYL SUZUKI CROSS-COUPLINGS OF PRIMARY ALKYL BROMIDES AT ROOM TEMPERATURE: (13-CHLOROTRIDECYLOXY)TRIETHYLSILANE (Silane, [(13-chlorotridecyl)oxy]triethyl-) Cross-coupling Preparation of Silane, [(13-chlorotridecyl)oxy]triethyl-. Submitted by Sha Lou and Gregory C. Fu1. DOI: 10.15227/orgsyn.087.0299. Organic Syntheses
PALLADIUM-CATALYZED COUPLING OF ACID CHLORIDES WITH ORGANOTIN REAGENTS: ETHYL (E)-4-(4-NITROPHENYL)-4-OXO-2-BUTENOATE (2-Butenoic acid, 4-(4-nitrophenyl)-4-oxo-, ethyl ester, (E)-) Cross-coupling Preparation of 2-Butenoic acid, 4-(4-nitrophenyl)-4-oxo-, ethyl ester, (E)-. Submitted by A. F. Renaldo1, J. W. Labadie, and J. K. Stille2. DOI: 10.15227/orgsyn.067.0086. Organic Syntheses
PALLADIUM-CATALYZED COUPLING OF VINYL TRIFLATES WITH ORGANOSTANNANES: 4-tert-BUTYL-1-VINYLCYCLOHEXENE AND 1-(4-tert-BUTYLCYCLOHEXEN-1-YL)-2-PROPEN-1-ONE (Cyclohexene, 4-(1,1-dimethylethyl)-1-ethenyl- and 2-propen-1-one, 1-[4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]) Cross-coupling Preparation of Cyclohexene, 4-(1,1-dimethylethyl)-1-ethenyl- and 2-propen-1-one, 1-[4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]. Submitted by William J. Scott1, G. T. Crisp2, and J. K. Stille3. DOI: 10.1… Organic Syntheses
PALLADIUM CATALYZED CROSS-COUPLING OF (Z)-1-HEPTENYLDIMETHYLSILANOL WITH 4-IODOANISOLE: (Z)-1-HEPTENYL)-4-METHOXYBENZENE (Benzene,1-(1Z)-1-heptenyl-4-methoxy-) Cross-coupling Preparation of Benzene,1-(1Z)-1-heptenyl-4-methoxy-. Submitted by Scott E. Denmark and Zhigang Wang1. DOI: 10.15227/orgsyn.081.0042. Organic Syntheses
PALLADIUM-CATALYZED CROSS-COUPLING USING AN AIR-STABLE TRIMETHYLALUMINUM SOURCE. PREPARATION OF ETHYL 4-METHYLBENZOATE Cross-coupling Preparation of PALLADIUM-CATALYZED CROSS-COUPLING USING AN AIR-STABLE TRIMETHYLALUMINUM SOURCE. PREPARATION OF ETHYL 4-METHYLBENZOATE. Submitted by Andrej Vinogradov and Simon Woodward1. DOI: 10.15227… Organic Syntheses
PLATINUM CATALYZED HYDROSILYLATION AND PALLADIUM CATALYZED CROSS-COUPLING: ONE-POT HYDROARYLATION OF 1-HEPTYNE TO (E)-1-(1-HEPTENYL)-4-METHOXYBENZENE (Benzene, 1-(1E)-1-heptenyl-4-methoxy-) Cross-coupling Preparation of Benzene, 1-(1E)-1-heptenyl-4-methoxy-. Submitted by Scott E. Denmark and Zhigang Wang1. DOI: 10.15227/orgsyn.081.0054. Organic Syntheses
Preparation of 1-Monoacylglycerols via the Suzuki-Miyaura Reaction: 2,3-Dihydroxypropyl (Z)-tetradec-7-enoate Cross-coupling Preparation of Preparation of 1-Monoacylglycerols via the Suzuki-Miyaura Reaction: 2,3-Dihydroxypropyl (Z)-tetradec-7-enoate. Submitted by Dexi Yang1, Valerie A. Cwynar1, David J. Hart1, Jakkam Madanm… Organic Syntheses
REDUCTIVE COUPLING OF CARBONYLS TO ALKENES: ADAMANTYLIDENEADAMANTANE (Tricyclo[3.3.1.13,7]decane, tricyclo[3.3.1.13,7]decylidene-) Cross-coupling Preparation of Tricyclo[3.3.1.13,7]decane, tricyclo[3.3.1.13,7]decylidene-. Submitted by Michael P. Fleming and John E. McMurry1. DOI: 10.15227/orgsyn.060.0113. Organic Syntheses
(S)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE IN NICKEL-CATALYZED ASYMMETRIC REDUCTIVE COUPLING OF ALKYNES AND ALDEHYDES: ENANTIOSELECTIVE SYNTHESIS OF ALLYLIC ALCOHOLS AND α-HYDROXY KETONES ((R)-Butan-2-one, 1-cyclohexyl, 1-hydroxy-) Cross-coupling Preparation of (R)-Butan-2-one, 1-cyclohexyl, 1-hydroxy-. Submitted by Aaron R. Van Dyke, Karen M. Miller, and Timothy F. Jamison1. DOI: 10.15227/orgsyn.084.0111. Organic Syntheses
Sonogashira coupling Cross-coupling The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond … Wikipedia: Category:Name reactions
STILLE COUPLINGS CATALYZED BY PALLADIUM-ON-CARBON WITH CuI AS A COCATALYST: SYNTHESIS OF 2-(4'-ACETYLPHENYL)THIOPHENE 1 Cross-coupling Preparation of STILLE COUPLINGS CATALYZED BY PALLADIUM-ON-CARBON WITH CuI AS A COCATALYST: SYNTHESIS OF 2-(4'-ACETYLPHENYL)THIOPHENE 1. Submitted by Lanny S. Liebeskind2 and Eduardo Peña-Cabrera3. DOI… Organic Syntheses
Stille reaction Cross-coupling The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as o… Wikipedia: Category:Name reactions
SULFIDE CONTRACTION via ALKYLATIVE COUPLING: 3-METHYL-2,4-HEPTANEDIONE (2,4-Heptanedione, 3-methyl-) Cross-coupling Preparation of 2,4-Heptanedione, 3-methyl-. Submitted by P. Loeliger1 and E. Flückiger2. DOI: 10.15227/orgsyn.055.0127. Organic Syntheses
Suzuki–Miyaura coupling: 4-bromobenzonitrile + phenylboronic acid → 4-cyanobiphenyl Scale Cross-coupling Canonical Pd(0)-catalysed cross-coupling of an aryl halide with an aryl boronic acid. The 4-cyanobiphenyl target is the textbook demonstration substrate — electron-poor aryl halide + electron-rich bor… Suzuki 1979
SUZUKI-MIYAURA CROSS-COUPLING: PREPARATION OF 2'-VINYLACETANILIDE (N-(2-Ethenylphenyl)acetamide) Cross-coupling Preparation of N-(2-Ethenylphenyl)acetamide. Submitted by Bertrand Cottineau, Albane Kessler, and Donal F. O'Shea1. DOI: 10.15227/orgsyn.083.0045. Organic Syntheses
Suzuki reaction Cross-coupling The Suzuki reaction or Suzuki coupling is an organic reaction that uses a palladium complex catalyst to cross-couple a boronic acid to an organohalide. It was first published in 1979 by Akira Suzuki, … Wikipedia: Category:Name reactions
Synthesis of 1,3-Dimethyl-3-(p-tolyl)-1H-pyrrolo[3,2-c]pyridin-2(3H)-one by Cu(II)-Mediated Direct Oxidative Coupling Cross-coupling Preparation of Synthesis of 1,3-Dimethyl-3-(p-tolyl)-1H-pyrrolo[3,2-c]pyridin-2(3H)-one by Cu(II)-Mediated Direct Oxidative Coupling. Submitted by Chandan Dey and E. Peter Kündig*1. DOI: 10.15227/orgs… Organic Syntheses
Synthesis of 2,3-Disubstituted Benzofurans by the Palladium-Catalyzed Coupling of 2-Iodoanisoles and Terminal Alkynes, Followed by Electrophilic Cyclization: 3-Iodo-2-phenylbenzofuran Cross-coupling Preparation of Synthesis of 2,3-Disubstituted Benzofurans by the Palladium-Catalyzed Coupling of 2-Iodoanisoles and Terminal Alkynes, Followed by Electrophilic Cyclization: 3-Iodo-2-phenylbenzofuran. … Organic Syntheses
SYNTHESIS OF (2R,3R)-2,3-DIMETHYL-1,4-BUTANEDIOL BY OXIDATIVE HOMOCOUPLING OF (4S)-ISOPROPYL-3-PROPIONYL-2-OXAZOLIDINONE (2,3-dimethylbutane-1,4-diol, (2R, 3R)-) Cross-coupling Preparation of 2,3-dimethylbutane-1,4-diol, (2R, 3R)-. Submitted by Chong-Dao Lu and Armen Zakarian1. DOI: 10.15227/orgsyn.085.0158. Organic Syntheses
SYNTHESIS OF 2-SUBSTITUTED BIARYLS VIA Cu/Pd-CATALYZED DECARBOXYLATIVE CROSS-COUPLING OF 2-SUBSTITUTED POTASSIUM BENZOATES: 4-METHYL-2'-NITROBIPHENYL AND 2-ACETYL-4'-METHYLBIPHENYL (Biphenyl, 4-Methyl-2'-nitro-) Cross-coupling Preparation of Biphenyl, 4-Methyl-2'-nitro-. Submitted by Lukas J. Gooßen1, Nuria Rodríguez, Christophe Linder, Bettina Zimmermann, and Thomas Knauber. DOI: 10.15227/orgsyn.085.0196. Organic Syntheses
SYNTHESIS OF 3-PYRIDYLBORONIC ACID AND ITS PINACOL ESTER. APPLICATION OF 3-PYRIDYLBORONIC ACID IN SUZUKI COUPLING TO PREPARE 3-PYRIDIN-3-YLQUINOLINE (Quinoline, 3-(3-pyridinyl)-) Cross-coupling Preparation of Quinoline, 3-(3-pyridinyl)-. Submitted by Wenjie Li, Dorian P. Nelson, Mark S. Jensen, R. Scott Hoerrner, Dongwei Cai, and Robert D. Larsen1. DOI: 10.15227/orgsyn.081.0089. Organic Syntheses

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