NiII, CuII and ZnII complexes with a sterically hindered scorpionate ligand (TpmsPh) and catalytic application in the diasteroselective nitroaldol (Henry) reaction

2014 ◽  
Vol 43 (40) ◽  
pp. 15192-15200 ◽  
Author(s):  
Bruno G. M. Rocha ◽  
Tatiana C. O. Mac Leod ◽  
M. Fátima C. Guedes da Silva ◽  
Konstantin V. Luzyanin ◽  
Luísa M. D. R. S. Martins ◽  
...  
Keyword(s):  
Coordination Mode ◽  
Henry Reaction ◽  
Catalytic Application ◽  
Nitroaldol Reaction ◽  
Sterically Hindered ◽  
Scorpionate Ligand

The bulky (TpmsPh)− adapts its coordination mode to the electronic and steric preferences of the NiII, CuII or ZnII centre forming complexes which catalyse the nitroaldol reaction.

Henry Reaction/Nitroaldol Reaction

2012 ◽  
pp. 1
Author(s):  
K. Hof ◽  
K. M. Lippert ◽  
P. R. Schreiner
Keyword(s):  
Henry Reaction ◽  
Nitroaldol Reaction

Water-Assisted Organocatalysis: An Enantioselective Green Protocol for the Henry Reaction

2013 ◽  
Vol 66 (6) ◽  
pp. 661 ◽  
Author(s):  
Prashant B. Thorat ◽  
Santosh V. Goswami ◽  
Wamanrao N. Jadhav ◽  
Sudhakar R. Bhusare
Keyword(s):  
Hydrogen Bonding ◽  
Room Temperature ◽  
Enantioselective Synthesis ◽  
Henry Reaction ◽  
Reaction Conditions ◽  
Green Protocol ◽  
Excellent Yield ◽  
Water As Solvent ◽  
Nitroaldol Reaction ◽  
Work Up

We report an enantioselective Henry (nitroaldol) reaction catalysed by an organocatalyst using water as solvent. The enantioselective synthesis of β-nitroalcohols was achieved by using a neutral chiral organocatalyst, through strong hydrogen bonding, which results in the formation of corresponding products in excellent yield and enantioselectivity at room temperature. Other attractive features of the method are the eco-friendly, non-hazardous, and mild reaction conditions, inexpensive catalyst, and simple work up conditions.

scholarly journals The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines

2008 ◽  
Vol 6 (4) ◽  
pp. 526-534 ◽  
Author(s):  
Michelle Guy ◽  
Sally Freeman ◽  
John Alder ◽  
Simon Brandt
Keyword(s):  
Nmr Spectroscopy ◽  
Aromatic Aldehyde ◽  
Spectroscopic Studies ◽  
Second Step ◽  
Reduction Step ◽  
Henry Reaction ◽  
Impurity Profile ◽  
Nitroaldol Reaction ◽  
By Products ◽  
Selection Of

AbstractA clandestine two-step route to psychoactive racemic phenylalkylamines utilises the Henry reaction. In the first step an aromatic aldehyde reacts with a nitroalkane to give the nitrostyrene intermediate. In the second step the nitrostyrene is reduced to the phenylalkylamine. An impurity profile of both steps was evaluated through the synthesis and analysis of common street derivatives. The formation of nitrile impurities in the nitroaldol reaction and hydroxylamine impurities in the reduction step were shown by NMR spectroscopy and GC-MS. A selection of reducing agents has been used to give the phenylalkylamines, together with variable quantities of the partially reduced hydroxylamine product. GC-MS analysis of the hydroxylamines showed heat-induced disproportionation which led to the detection of the corresponding oximes.

Synthesis and characterization of chiral recyclable dimeric copper(ii)–salen complexes and their catalytic application in asymmetric nitroaldol (Henry) reaction

2014 ◽  
Vol 4 (2) ◽  
pp. 411-418 ◽  
Author(s):  
Anjan Das ◽  
Rukhsana I. Kureshy ◽  
P. S. Subramanian ◽  
Noor-ul H. Khan ◽  
Sayed H. R. Abdi ◽  
...  
Keyword(s):  
Synthesis And Characterization ◽  
Henry Reaction ◽  
Catalytic Application ◽  
Salen Complexes

Asymmetric nitroaldol reaction with a chiral copper complex derived from D-tartaric acid

2008 ◽  
Vol 86 (3) ◽  
pp. 261-263 ◽  
Author(s):  
Changsheng Gan
Keyword(s):  
Tartaric Acid ◽  
Copper Complex ◽  
Henry Reaction ◽  
Nitroaldol Reaction

A novel catalytic enantioselective Henry reaction has been developed using a tetradentate copper complex derived from D-tartaric acid to give β-nitroalkanols in moderate to high enantioselectivities.Key words: Henry reaction, D-tartaric acid, enantioselective, β-nitroalkanols.

Zinc amidoisophthalate complexes and their catalytic application in the diastereoselective Henry reaction

2015 ◽  
Vol 39 (4) ◽  
pp. 3004-3014 ◽  
Author(s):  
Anirban Karmakar ◽  
M. Fátima C. Guedes da Silva ◽  
Susanta Hazra ◽  
Armando J. L. Pombeiro
Keyword(s):  
Heterogeneous Catalysts ◽  
Henry Reaction ◽  
Catalytic Application

5-Propionamidoisophthalic acid and 5-benzamidoisophthalic acid are used to synthesize new zinc(ii) complexes which act as heterogeneous catalysts for the diastereoselective nitroaldol (Henry) reaction.

Approaches to alkane functionalization with Tp′Pt and (nacnac)Pt reagents

2009 ◽  
Vol 87 (1) ◽  
pp. 288-296 ◽  
Author(s):  
Nathan M West ◽  
Joseph L Templeton
Keyword(s):  
Oxidation State ◽  
Coordination Mode ◽  
Reductive Elimination ◽  
Binding Modes ◽  
Acid Base ◽  
The Past ◽  
Alkane Functionalization ◽  
Tightly Coupled ◽  
Scorpionate Ligand ◽  
Alkyl Hydrides

In this perspective article we give an overview of our studies of C–H activation with platinum over the past decade. The scorpionate ligand Tp′ (Tp′ = hydrotris(3,5-dimethylpyrazolyl)borate) has exhibited the ability to stabilize both Pt(IV) and Pt(II) complexes due to flexibility between κ3 and κ2 binding modes. Control of the Tp′ coordination mode and Pt oxidation state is tightly coupled with acid/base chemistry. This ability allowed us to model a spectrum of intermediates in C–H activation reactions, including Pt(IV) alkyl hydrides, five-coordinate Pt(IV) silyl hydrides, and Pt(II) benzene complexes. We have been able to observe sturdy Pt(II) benzene complexes and probe their equilibria with the respective C–H activated Pt(IV) species in the presence of an added ligand. We have also taken steps toward functionalizing hydrocarbons with Tp′Pt by dehydrogenation of alkanes and by arylation of olefins. We have recently turned to bidentate nacnac (nacnac = N-phenyl-β-enamineimine) ligands in the hopes of catalytically functionalizing hydrocarbons.Key words: C–H activation, reductive elimination, Tp′Pt, five-coordinate, β-diiminate.

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