Inside Cover: Identification of a Higher‐Order Organozincate Intermediate Involved in Negishi Cross‐Coupling Reactions by Mass Spectrometry and NMR Spectroscopy (Chem. Eur. J. 28/2011)

2011 ◽  
Vol 17 (28) ◽  
pp. 7706-7706
Author(s):  
Howard N. Hunter ◽  
Niloufar Hadei ◽  
Voislav Blagojevic ◽  
Pascal Patschinski ◽  
George T. Achonduh ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Cross Coupling ◽  
Higher Order ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Identification of a Higher‐Order Organozincate Intermediate Involved in Negishi Cross‐Coupling Reactions by Mass Spectrometry and NMR Spectroscopy

2011 ◽  
Vol 17 (28) ◽  
pp. 7845-7851 ◽  
Author(s):  
Howard N. Hunter ◽  
Niloufar Hadei ◽  
Voislav Blagojevic ◽  
Pascal Patschinski ◽  
George T. Achonduh ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Cross Coupling ◽  
Higher Order ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

scholarly journals Argentate(i) and (iii) complexes as intermediates in silver-mediated cross-coupling reactions

2018 ◽  
Vol 54 (40) ◽  
pp. 5086-5089 ◽  
Author(s):  
Sebastian Weske ◽  
Richard A. Hardin ◽  
Thomas Auth ◽  
Richard A. J. O’Hair ◽  
Konrad Koszinowski ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Esi Mass Spectrometry

Silver-mediated cross-coupling reactions proceed via anionic ate complexes, which have been characterized by a combination of NMR spectroscopy, ESI mass spectrometry, and quantum-chemical calculations.

Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks

Synthesis ◽  
2018 ◽  
Vol 50 (10) ◽  
pp. 2009-2018
Author(s):  
Jan-Hendrik Lamm ◽  
Philipp Niermeier ◽  
Leif Körte ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Building Block ◽  
High Resolution Mass Spectrometry ◽  
Cross Coupling ◽  
Easy Access ◽  
Coupling Reactions ◽  
X Ray Diffraction ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
Resolution Mass

An easy access to 1,8-dichloro-10-(ethynyl)anthracene is reported, which is widely applicable for building up rigid linkers between two 1,8-dichloroanthracene units. For this, 1,8-dichloroanthren-10(9H)-one was reacted with ethynylmagnesium bromide in the presence of CeCl3; the yield was 65%. This building block was used as a substrate in (cross-)coupling reactions and some examples of linked 1,8-dichloroanthracen-10-yls (e.g., 1,8-bis[(1,8-dichloroanthracen-10-yl)-ethynyl]naphthalene or 1,2-bis[(1,8-dichloroanthracen-10-yl)ethynyl]-benzene) were synthesized in good to moderate yields. Linked 1,8-dichloroanthracen-10-yl derivatives were also synthesized by cross-coupling reactions using 10-bromo-1,8-dichloroanthracene and doubly ethynyl-substituted substrates. Linkers between the 1,8-dichloroanthracene units were: butadiynediyl, dimethylsilyldiethynyl, octa-1,7-diyne-1,8-diyl, propane-1,3-diylbis(dimethylsilyl)diethynyl, benzene-1,2-diethynyl, naphthalene-1,8-diyldiethynyl, and anthracene-1,8-diyldiethynyl. The new anthracene compounds were characterized by NMR spectroscopy, high-resolution mass spectrometry, and, in part, by X-ray diffraction experiments.

scholarly journals Synthesis and X-ray Diffraction Study of thiosemicarbazone Palladacycles with dppm

Proceedings ◽  
2021 ◽  
Vol 62 (1) ◽  
pp. 13
Author(s):  
Marcos Rúa-Sueiro ◽  
Paula Munin-Cruz ◽  
Francisco Reigosa ◽  
José M. Vila ◽  
Juan M. Ortigueira
Keyword(s):  
Nmr Spectroscopy ◽  
31P Nmr ◽  
Antimicrobial Agents ◽  
Cross Coupling ◽  
31P Nmr Spectroscopy ◽  
Coupling Reactions ◽  
X Ray Diffraction ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
Platinum Salt

Cyclometallated compounds have been extensively studied, in particular those with palladium and platinum. This is because of their possible applications in medicinal chemistry, as anticancer or antimicrobial agents; in some cases, with similar results as cisplatin, carboplatin or oxaliplatin. What is also remarkable is their use as homogeneous catalysts, for example, in cross coupling reactions such as Suzuki–Miyaura or Mizoroki–Heck. Herein, we report the synthesis of different thiosemicarbazone ligands, which will be reacted with a palladium or platinum salt, to give the corresponding cyclometallated compounds; in addition, their reactivity with bis(diphenylphosphino)methane (dppm) will be studied. Characterization has been carried out by elemental analysis, IR spectroscopy, 1H and 31P NMR spectroscopy. Additionally, 1c has been studied by X-ray diffraction.

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

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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