Nitrosonium-Mediated Phenol–Arene Cross-Coupling Involving Direct C–H Activation

2017 ◽  
Vol 70 (4) ◽  
pp. 407 ◽  
Author(s):  
Anna Eisenhofer ◽  
Uta Wille ◽  
Burkhard König
Keyword(s):  
Cross Coupling ◽  
Solvent System ◽  
Environmentally Benign ◽  
Lithium Nitrate ◽  
Coupling Reactions ◽  
Substituted Phenols ◽  
Cross Coupling Reactions ◽  
Inorganic Nitrate ◽  
Nitrosonium Ion

The nitrosonium ion (NO+) is a highly versatile nitration and nitrosation reagent, as well as a strong one-electron oxidant. Herein, we describe an environmentally benign and mild method for the in situ formation of NO+ from readily available inorganic nitrate salts, i.e. lithium nitrate, through a finely tuned interplay between formic acid and MeOH, which are used as the solvent system. This methodology was applied to the NO+-induced oxidative C–H activation of methoxy-substituted phenols, which are versatile lignin-derived aromatic feedstocks, to achieve C–C cross-coupling reactions with arenes. The regeneration of NO+ by atmospheric molecular oxygen enables substoichiometric use of the nitrate.

Nitrile-functionalized pyrrolidinium ionic liquids as solvents for cross-coupling reactions involving in situ generated nanoparticlecatalyst reservoirs

2010 ◽  
Vol 12 (8) ◽  
pp. 1834-1841 ◽  
Author(s):  
Yugang Cui ◽  
Ilaria Biondi ◽  
Manish Chaubey ◽  
Xue Yang ◽  
Zhaofu Fei ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Ni(COD)(DMFU): A Heteroleptic 16-Electron Precatalyst for 1,2-Diarylation of Alkenes

Synlett ◽  
2021 ◽  
Author(s):  
Nana Kim ◽  
Van T. Tran ◽  
Omar Apolinar ◽  
Steven Wisniewski ◽  
Martin Eastgate ◽  
...  
Keyword(s):  
Nickel Complex ◽  
Active Catalyst ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Coupling Reactions ◽  
Beneficial Effects ◽  
Cross Coupling Reactions ◽  
Growing Body ◽  
Hydride Elimination

Electron-deficient olefin (EDO) ligands are known to promote a variety of nickel-catalyzed cross-coupling reactions, presumably by accelerating the reductive elimination step and preventing undesired β-hydride elimination. While there is a growing body of experimental and computational evidence elucidating the beneficial effects of EDO ligands, significant gaps remain in our understanding of the underlying coordination chemistry of the Ni–EDO species involved. In particular, most procedures rely on in situ assembly of the active catalyst, and there is a paucity of pre-ligated Ni-EDO precatalysts. Herein, we investigate the 16-electron, heteroleptic nickel complex, Ni(COD)(DMFU), and examine the performance of this complex as a precatalyst in 1,2-diarylation of alkenes.

ChemInform Abstract: Suzuki-Miyaura Cross-Coupling Reactions in Water Using in situ Generated Palladium(II)-Phosphazane Complexes.

ChemInform ◽  
2014 ◽  
Vol 45 (28) ◽  
pp. no-no
Author(s):  
Mojtaba Amini ◽  
Abbas Tarassoli ◽  
Saeed Yousefi ◽  
Sepideh Delsouz-Hafshejani ◽  
Mina Bigdeli ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

scholarly journals Recyclable glucose-derived palladium(0) nanoparticles as in situ-formed catalysts for cross-coupling reactions in aqueous media

RSC Advances ◽  
2016 ◽  
Vol 6 (20) ◽  
pp. 16115-16121 ◽  
Author(s):  
Jason E. Camp ◽  
Jay J. Dunsford ◽  
Oliver S. G. Dacosta ◽  
Rebecca K. Blundell ◽  
James Adams ◽  
...  
Keyword(s):  
Aqueous Solutions ◽  
Aqueous Media ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Renewable sugar-derived palladium(0) nanoparticles (PdNPs) are effective as in situ formed catalysts for cross-coupling reactions in aqueous solutions.

Suzuki–Miyaura cross-coupling reactions in water using in situ generated palladium(II)–phosphazane complexes

2014 ◽  
Vol 25 (1) ◽  
pp. 166-168 ◽  
Author(s):  
Mojtaba Amini ◽  
Abbas Tarassoli ◽  
Saeed Yousefi ◽  
Sepideh Delsouz-Hafshejani ◽  
Mina Bigdeli ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

scholarly journals Regioselective Synthesis of New 2,4-(Het)aryl-3H-pyrido[1′,2′:1,5]pyrazolo[4,3-d]pyrimidines Involving Palladium-Catalyzed Cross-Coupling Reactions

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2740 ◽  
Author(s):  
Abdelaziz Ejjoummany ◽  
Rabia Belaroussi ◽  
Ahmed El Hakmaoui ◽  
Mohamed Akssira ◽  
Gérald Guillaumet ◽  
...  
Keyword(s):  
Process Optimization ◽  
Cross Coupling ◽  
Regioselective Synthesis ◽  
Coupling Reactions ◽  
Pyrimidine Derivatives ◽  
Release Process ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
High Yields

The design of some novel di-(het)arylated-3H-pyrido[1′,2′:1,5]pyrazolo[4,3-d]pyrimidine derivatives is reported. The series was developed from 1-aminopyridinium iodide, which afforded the key intermediate bearing two thiomethyl and amide functions, each of them useful for palladium catalyzed cross coupling reactions by alkyl sulfur release and C-O activation, respectively. The two regioselective and successive cross-coupling reactions were first carried out in C-4 by in situ C-O activation and next in C-2 by a methylsulfur release. Process optimization furnished conditions leading to products in high yields. The scope and limitations of the methodologies were evaluated and the final compounds characterized.

ChemInform Abstract: One-Pot Negishi Cross-Coupling Reactions of in situ Generated Zinc Reagents with Aryl Chlorides, Bromides, and Triflates.

ChemInform ◽  
2009 ◽  
Vol 40 (5) ◽  
Author(s):  
Shohei Sase ◽  
Milica Jaric ◽  
Albrecht Metzger ◽  
Vladimir Malakhov ◽  
Paul Knochel
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions
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