scholarly journals Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Styrenes

Author(s):  
Jichao Xiao ◽  
John Montgomery

A simple procedure is reported for the nickel-catalyzed defluorinative alkylation of unactivated aliphatic aldehydes. The process involves the catalytic reductive union of trifluoromethyl styrenes with aldehydes using a nickel complex of a 6,6’-disubstituted bipyridine ligand with zinc metal as the terminal reductant. The protocol is distinguished by its broad substrate scope, mild conditions, and simple catalytic setup. Reaction outcomes are consistent with the intermediacy of an alpha-silyloxy(alkyl)nickel intermediate generated by a low-valent nickel catalyst, silyl electrophile, and the aldehyde substrate. Mechanistic findings with cyclopropanecarboxaldehyde provide insights into nature of the reactive intermediates and illustrate fundamental reactivity differences that are governed by subtle changes in ligand and substrate structure.

2011 ◽  
Vol 40 (9) ◽  
pp. 1036-1038 ◽  
Author(s):  
Shinya Nagao ◽  
Taisuke Matsumoto ◽  
Yuji Koga ◽  
Kouki Matsubara

2014 ◽  
Vol 18 (6) ◽  
pp. 1022-1027 ◽  
Author(s):  
Mohamed F. Abdel-Megeed ◽  
Mohamed M. Azaam ◽  
Gamal A. El-Hiti

2021 ◽  
Author(s):  
Vladimir Alekseevich Dodonov ◽  
Olga Kushnerova ◽  
Evgeny V Baranov ◽  
Alexander S. Novikov ◽  
Igor Leonidovich Fedushkin

Activation of carbon dioxide in mild conditions by metallylene [(dpp-bian)GaNa(DME)2] (dpp-bian = 1,2-bis[(2,6-di-iso¬propyl-phenyl)-imino]acenaphthene) is described. Further reaction of the activation complex [(dpp-bian)Ga(CO2)2Ga(dpp-bian)][Na(DME)2]2 (2) with diphenylketene, cyclohexylisocyanate, phenylisocyanate leads to elimination...


2020 ◽  
Vol 11 (19) ◽  
pp. 5043-5051
Author(s):  
Jian Yang ◽  
Verònica Postils ◽  
Michael I. Lipschutz ◽  
Meg Fasulo ◽  
Christophe Raynaud ◽  
...  

A cationic nickel complex of the bis(8-quinolyl)(3,5-di-tert-butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl]+, is a precursor to efficient catalysts for the hydrosilation of alkenes with hydrosilanes under mild conditions and low catalyst loadings.


Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2891-2896 ◽  
Author(s):  
Jinna Song ◽  
Xihe Bi ◽  
Qi Zhang ◽  
Kaki Raveendra Babu ◽  
Zhouliang Huang

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.


2008 ◽  
Vol 61 (11) ◽  
pp. 905 ◽  
Author(s):  
Shivaji S. Pawar ◽  
Deepak V. Dekhane ◽  
Murlidhar S. Shingare ◽  
Shivaji N. Thore

Alum (KAl(SO4)2·12H2O) performs as a novel catalyst for the synthesis of 2-arylbenzothiazoles and 2-arylbenzoxazole from o-aminothiophenol and o-aminophenol with various substituted aldehydes in good to excellent isolated yields (85–95%) using water as a solvent at ambient temperature. Several solvents were examined for this reaction; however, in terms of reaction yield and time, water was found to be the optimum solvent. The remarkable advantages offered by this method are an inexpensive and easily available catalyst, a simple procedure, mild conditions, much faster (60–90 min) reactions, and good to excellent yields of products.


2002 ◽  
Vol 2002 (6) ◽  
pp. 253-254 ◽  
Author(s):  
Shyam Rele ◽  
Asoke Banerji ◽  
Sanjay Talukdar

A simple procedure for reductive amination of aliphatic carbonyls, giving direct access to free primary amines using low–valent titanium (LVT) reagent has been reported.


2019 ◽  
Author(s):  
Yichen Wu ◽  
Tao liu ◽  
Dongping Chen ◽  
Daoming Wang ◽  
Peng Wang

Herein, we reported a nickel catalyzed hydrogenation of alkenes with water as the sole hydrogen source. Employing Zn as reductant and water as solvent in the presence of a catalytic amount of nickel catalyst led to direct hydrogenation of a series of electron-rich and electron-deficient alkenes in high yields. This protocol features unprecedented heterocycle and functional group tolerance under facile and mild conditions. Selective hydrogenation of the substrates containing additional reducible functionalities, such as alkenyl, alkynyl, chloride, ketone, and benzyl group etc, was also realized.


2010 ◽  
Vol 46 (28) ◽  
pp. 5115 ◽  
Author(s):  
María J. Romero ◽  
Rosa Pedrido ◽  
Ana M. González-Noya ◽  
Miguel Martínez-Calvo ◽  
Guillermo Zaragoza ◽  
...  

RSC Advances ◽  
2014 ◽  
Vol 4 (50) ◽  
pp. 26491-26498 ◽  
Author(s):  
R. Villanneau ◽  
A. Roucoux ◽  
P. Beaunier ◽  
D. Brouri ◽  
A. Proust

Metallic palladium nanoparticles have been generated by hydrogenation in very mild conditions of aqueous solutions of non-organometallic PdII-derivatives of heteropolytungstates.


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