Fluorine-Containing Allenylpalladium Complexes. Synthesis of Optically Active Fluoroalkylated Allenes and Furan Derivatives

2002 ◽  
Vol 67 (10) ◽  
pp. 1421-1435 ◽  
Author(s):  
Tsutomu Konno ◽  
Mitsuru Tanikawa ◽  
Takashi Ishihara ◽  
Hiroki Yamanaka
Keyword(s):  
Palladium Catalyst ◽  
Coupling Reaction ◽  
Diethyl Malonate ◽  
Enantiomeric Purity ◽  
Optically Active ◽  
The Other ◽  
Methyl Acetoacetate ◽  
Furan Derivatives ◽  
Dicarbonyl Compounds ◽  
High Yields

The reaction of fluoroalkylated propargyl mesylates with various nucleophiles, such as zinc reagents and enolates derived from 1,3-dicarbonyl compounds, in the presence of a palladium catalyst was investigated in detail. Various zinc reagents participated in the coupling reaction to give the corresponding fluoroalkylated allenes in good yields. When chiral mesylates were employed, the corresponding optically active allenes were obtained without any loss of enantiomeric purity in the reaction. On the other hand, treatment of trifluoromethylated propargyl mesylate with stabilized carbanions derived from methyl acetoacetate, acetylacetone, and diethyl malonate afforded fluorine-containing furan derivatives in moderate to high yields.

Synthesis of Cyclic 3-Aryl-Substituted 1,2-Dicarbonyl Compounds via Suzuki Cross-Coupling Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (09) ◽  
pp. 1883-1890 ◽  
Author(s):  
Margus Lopp ◽  
Eleana Lopušanskaja ◽  
Anne Paju ◽  
Ivar Järving
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Dicarbonyl Compounds ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
High Yields

A method for the synthesis of cyclic 3-aryl- and heteroaryl-substituted 1,2-dicarbonyl compounds with different ring sizes by using a Suzuki cross-coupling reaction between 3-halo-1,2-dicarbonyl compounds and arylboronic acids is developed. The 3-halo-1,2-dicarbonyl substrates are easily available from 1,2-dicarbonyl compounds. The method is versatile, affording good to high yields of the target compounds.

Synthesis of terminal arylacetylenes by a Stille coupling reaction catalysed by a MCM-41-supported bidentate phosphine palladium(O) complex

2008 ◽  
Vol 2008 (11) ◽  
pp. 615-618 ◽  
Author(s):  
Wenyan Hao ◽  
Yue Wang ◽  
Shouri Sheng ◽  
Mingzhong Cai
Keyword(s):  
Aqueous Medium ◽  
Palladium Catalyst ◽  
Basic Problem ◽  
Coupling Reaction ◽  
Aryl Halides ◽  
Stille Coupling ◽  
Bidentate Phosphine ◽  
Stille Coupling Reaction ◽  
High Yields ◽  
Mcm 41

A variety of terminal arylacetylenes have been conveniently synthesised in good to high yields by Stille coupling of aryl halides with ethynyltributylstannane catalysed by a MCM-41-supported bidentate phosphine palladium(O) complex in an aqueous medium and under air. Our system not only avoids the requirement for water-free and oxygen-free conditions, but also solves the basic problem of palladium catalyst reuse.

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

Hydroxyl-containing bis(sulfonates). Reaction of 1,4-dibromo-2,3-butanedione with water, methanol and sodium sulfite

2021 ◽  
pp. 1-12
Author(s):  
Gerasimos M. Tsivgoulis ◽  
Dimitris G. Vachliotis ◽  
Golfo G. Kordopati ◽  
Panayiotis V. Ioannou
Keyword(s):  
13C Nmr ◽  
Sodium Sulfite ◽  
The Other ◽  
Carbonyl Carbon ◽  
1H And 13C Nmr ◽  
Sodium Sulfonate ◽  
Pure Product ◽  
Methylene Groups ◽  
New Type ◽  
High Yields

Sulfonates are well-known substances with a variety of applications, e.g. as surfactants. On the other hand, bis(sulfonates) bearing hydroxyl or keto group(s) in between the sulfonate groups can be used with or without further modification as starting materials for the preparation of new type of molecules capable to form either complexes or in general supramolecular structures. The synthesis of three hydroxyl-bearing bis(sulfonates), 2-hydroxypropane-1,3-bis(sodium sulfonate) 4, DL-2,3-dihydroxybutane-1,4-bis(sodium sulfonate) 8, and sodium 2,3,4-trihydroxy-1-sulfonate 7 (as by-product) via the Strecker sulfonation are described. Interestingly, under similar conditions, sulfonation of 1,4-dibromo-2,3-butanedione 9 was found to be very complicated and no pure product could be isolated, despite previously reported results on sulfonation of α-halogenated ketones in high yields. There are indications that SO3 2 -  attacks at the carbonyl carbon of 9 followed by rearrangement and expulsion of SO4 2 - . 1,4-dibromo-2,3-butanedione 9, bearing two keto groups next to methylene groups, can potentially exist as enols or in the case of its solution in hydroxylic solvents in the form of hemiketals or geminal diols. This behavior of 9 when is dissolved in CDCl3, CD3OD and D2O was studied by means of UV-Vis, 1H and 13C NMR and the nature of the adducts formed was elucidated.

scholarly journals Synthesis of N-alkoxyphthalimide derivatives via PIDA-promoted cross dehydrogenative coupling reaction

RSC Advances ◽  
2021 ◽  
Vol 11 (14) ◽  
pp. 8051-8054
Author(s):  
Rongxiang Chen ◽  
Bing Liu ◽  
Wenbo Li ◽  
Kai-Kai Wang ◽  
Changqing Miao ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Dehydrogenative Coupling ◽  
Aryl Ketones ◽  
High Yields

A cross dehydrogenative coupling reaction of aryl ketones with N-hydroxyphthalimide was realized. The reactions afforded a clean and facile access to diverse N-alkoxyphthalimide derivatives in high yields (up to 99%).

Umpolung Coupling of Pyridine-2-carboxaldehydes and Propargylic Carbonates via N-Heterocyclic Carbene/Palladium Synergetic Catalysis

2021 ◽  
Author(s):  
Weiyang Bi ◽  
Yunhui Yang ◽  
Song Ye ◽  
Congyang Wang
Keyword(s):  
Palladium Catalyst ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cooperative Catalysis ◽  
Cross Coupling Reaction ◽  
First Time

The umpolung cross-coupling reaction of pyridine-2-carboxaldehydes and propargylic carbonates has been developed for the first time through N-heterocyclic carbene/palladium cooperative catalysis with the judicious selections of the palladium catalyst, ligand...

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