Palladium-catalyzed Suzuki cross-couplings of N′-mesyl arylhydrazines via C–N bond cleavage

RSC Advances ◽  
2014 ◽  
Vol 4 (49) ◽  
pp. 25576-25579 ◽  
Author(s):  
He-Ping Zhou ◽  
Jin-Biao Liu ◽  
Jian-Jun Yuan ◽  
Yi-Yuan Peng
Keyword(s):  
Boronic Acid ◽  
Bond Cleavage ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Mild Conditions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Aryl Boronic Acid ◽  
Biaryl Compounds

An efficient palladium-catalyzed Suzuki cross-coupling reaction of N′-mesyl arylhydrazine with aryl boronic acid is described, which affords the corresponding biaryl compounds in high yields. This transformation proceeds through C–N bond cleavage under mild conditions.

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>

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

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
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.

scholarly journals Recent Advances in the Applications of the Intramolecular Suzuki Cross-coupling Reaction in Cyclization and Heterocyclization: An Update

2020 ◽  
Vol 23 (22) ◽  
pp. 2469-2488 ◽  
Author(s):  
Majid M. Heravi ◽  
Masoumeh Malmir ◽  
Razieh Moradi
Keyword(s):  
Organic Chemistry ◽  
Boronic Acid ◽  
Heterocyclic Compounds ◽  
Aryl Halide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthetic Organic Chemistry ◽  
Previous Review ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

: The palladium-catalyzed reaction of aryl halide and boronic acid for the formation of C–C bonds so-called Suzuki–Miyaura cross-coupling reaction has many applications in Modern Synthetic Organic Chemistry. In 2013, we emphasized the applications of the intramolecular Suzuki cross-coupling reaction in cyclization and heterocyclization. Due to a plethora relevant papers appeared in the chemical literature, herein, we wish to cover by updating our previous review, the applications of the intramolecular Suzuki cross-coupling reaction in cyclization and heterocyclization leading to various homocyclic and heterocyclic compounds reported during a period of 2013 to 2018.

One-pot synthesis of benzoxaborole derivatives from the palladium-catalyzed cross-coupling reaction of alkoxydiboron with unprotected o-bromobenzylalcohols

2015 ◽  
Vol 13 (46) ◽  
pp. 11362-11368 ◽  
Author(s):  
Jianan Zhu ◽  
Ying Wei ◽  
Dongqing Lin ◽  
Changjin Ou ◽  
Linghai Xie ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

Under very mild conditions, functionalized benzoxaborole derivatives were prepared in good to excellent yields via a palladium-catalyzed Miyaura borylation reaction of readily available unprotected o-bromobenzylalcohols, and bis(pinacolato)diboron (B2pin2) without the assistance of an acid.

scholarly journals 2′-Chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine

Molbank ◽  
10.3390/m1040 ◽  
2018 ◽  
Vol 2019 (1) ◽  
pp. M1040 ◽  
Author(s):  
Dhafer Zinad ◽  
Dunya AL-Duhaidahaw ◽  
Ahmed Al-Amiery
Keyword(s):  
Mass Spectrometry ◽  
Boronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Gas Chromatography Mass Spectrometry ◽  
Target Compound ◽  
Chromatography Mass Spectrometry ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Layer Chromatography

The compound 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine was obtained with a good yield by the reaction of 2-chloro-4-(1-methyl-1H-imidazol-2-yl)pyridine with (2-chloropyridin-4-yl)boronic acid and structurally characterized by nuclear magnetic resonance (1H-NMR and 13C-NMR), thin-layer chromatography–mass spectrometry (TLC–MS), HPLC, gas chromatography–mass spectrometry (GC–MS), and elemental analysis. The functionalization of the pyridine was achieved by the palladium-catalyzed Suzuki–Miyaura carbon–carbon cross-coupling reaction that afforded the target compound.

2,3,2′,3′-Tetramethylbiphenyl

2006 ◽  
Vol 62 (5) ◽  
pp. o2012-o2013
Author(s):  
Wei Zheng ◽  
Hong-Jun Zhu ◽  
Yi Qian ◽  
Yi-Zu Wu
Keyword(s):  
Crystal Structure ◽  
Intermolecular Interactions ◽  
Title Compound ◽  
Boronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Twofold Axis ◽  
Compound C ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

The title compound, C16H18, was synthesized by a palladium-catalyzed boronic acid cross-coupling reaction. A crystallographic twofold axis passes through the mid-point of the C—C bond connecting the two rings. In the crystal structure, two fairly close C—H...π(arene) contacts appear to be the only significant intermolecular interactions.

scholarly journals 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.

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