Suzuki-Miyaura cross-coupling reaction with potassium aryltrifluoroborate in pure water using recyclable nanoparticle catalyst

This paper describes the Suzuki-Miyaura cross coupling reaction of aryl bromides with potassium aryltrifluoroborates in water catalyzed by linear polystyrene-stabilized PdO nanoparticles (PS-PdONPs). The reaction of aryl bromides having electron withdrawing groups or electron donating groups took place smoothly to give the corresponding coupling product in high yields. The catalyst recycles five times without significant loss of catalytic activity although a little bit increase in size of Pd NPs was observed after the reaction.

Download Full-text

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

10.26434/chemrxiv.12367334.v1 ◽

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

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 (DEST » -64 cm–1) or triplet ground state (DEST ³ 25 and 100 cm–1), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin S = 1 chains of organic diradicals with intrachain ferromagnetic coupling of J′/kB from 3 to 6 K.

Download Full-text

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

10.26434/chemrxiv.12582284.v1 ◽

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.

Download Full-text

Synthesis and Application of Tetrafluoroethylene (CF2CF2)-Containing Acetylene Derivatives

Synthesis ◽

10.1055/s-0039-1691744 ◽

2020 ◽

Vol 52 (13) ◽

pp. 1947-1958

Author(s):

Tsutomu Konno ◽

Gen Egashira ◽

Chihiro Kajimoto ◽

Takuto Kataoka ◽

Shigeyuki Yamada

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Alder Reaction ◽

Diels Alder ◽

Benzene Derivatives ◽

Diels Alder Reaction ◽

Cross Coupling Reaction ◽

Oxidative Aromatization ◽

High Yields ◽

Acetylene Derivatives

On treating 1,3,4-tribromo-1,1,2,2-tetrafluorobutane, readily prepared from commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene, with 3.3 equivalents of LHMDS at 0 °C in THF, the corresponding lithium acetylide could be prepared quantitatively. The acetylide reacted well with various aldehydes, ketones, or chlorosilanes to give the corresponding acetylene derivatives in high yields. It was also found that various iodoarenes could participate in the cross-coupling reaction with the zinc acetylide, readily prepared from the lithium acetylide and ZnCl2·TMEDA complex, in the presence of Pd(PPh3)4 to bring about the adducts in high yields. Thus-obtained acetylene derivatives underwent smooth Diels–Alder reaction with various 1,3-dienes to afford the corresponding 1,4- or 1,3-cyclohexadiene derivatives. In addition, it was revealed that the oxidative aromatization of the resulting cyclohexadiene derivatives with DDQ took place very smoothly, providing the multi-substituted benzene derivatives having a tetrafluoroethylene group.

Download Full-text

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽

10.1055/s-0039-1690895 ◽

2020 ◽

Vol 52 (16) ◽

pp. 2387-2394 ◽

Cited By ~ 1

Author(s):

Jorge A. Cabezas ◽

Natasha Ferllini

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Coupling Reactions ◽

Terminal Alkyne ◽

Copper Iodide ◽

Reaction Conditions ◽

Cross Coupling Reactions ◽

Cross Coupling Reaction ◽

Palladium Catalyzed ◽

High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

Download Full-text

Palladium-Schiff-base-silica framework as a robust and recyclable catalyst for Suzuki–Miyaura cross-coupling in aqueous media

RSC Advances ◽

10.1039/c5ra01574j ◽

2015 ◽

Vol 5 (48) ◽

pp. 38085-38092 ◽

Cited By ~ 16

Author(s):

Tahshina Begum ◽

Manoj Mondal ◽

Pradip K. Gogoi ◽

Utpal Bora

Keyword(s):

Schiff Base ◽

Catalytic Activity ◽

Room Temperature ◽

Aqueous Media ◽

Coupling Reaction ◽

Cross Coupling ◽

Recyclable Catalyst ◽

Cross Coupling Reaction

A novel Pd@imine-SiO2 catalyst was prepared and found to exhibit excellent catalytic activity in a Suzuki-Miyaura cross-coupling reaction under aqueous media at room temperature.

Download Full-text