scholarly journals Synthesis of multi-substituted indene derivatives from aryl, vinyl, and alkyl/aryl carbinols

2019 ◽  
Author(s):  
Mithun Chakraborty ◽  
Gaddam Mahesh ◽  
Omkar R Nakel ◽  
Gautamee Chavda ◽  
Susarla Anusha ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Nucleophilic Reagent ◽  
Acid Catalyst ◽  
Vinyl Ketone ◽  
Alkyl Aryl ◽  
Excellent Yield ◽  
Nucleophilic Addition Reaction ◽  
Lewis Acid Catalyst

A divergent approach to highly substituted functionalized indenes has been developed. The two-step reaction involving nucleophilic addition reaction of aryl vinyl ketone, an ideal intermediate with aryl or alkyl nucleophilic reagent, followed by electrocyclization (Nazarov cyclization) in the presence of Lewis acid catalyst afforded indene derivatives in good to excellent yield.

Nucleophilic addition reaction of aromatic compounds with α-chloroglycidates in the presence of Lewis acid

Tetrahedron ◽  
2003 ◽  
Vol 59 (10) ◽  
pp. 1781-1790 ◽  
Author(s):  
Jing-Rong Lin ◽  
Aidar T Gubaidullin ◽  
Vakhid A Mamedov ◽  
Sadao Tsuboi
Keyword(s):  
Lewis Acid ◽  
Aromatic Compounds ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Nucleophilic Addition Reaction

Kinetics of Reactions of 9-Isothiocyanatoacridine with Aromatic and Aliphatic Amines and Fluorescence Properties of the 1-Acridin-9-yl-3-alkyl(aryl)thioureas Obtained

1994 ◽  
Vol 59 (12) ◽  
pp. 2632-2640 ◽  
Author(s):  
Dana Mazagová ◽  
Pavol Kristian ◽  
Gejza Suchár ◽  
Ján Imrich ◽  
Marián Antalík
Keyword(s):  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Spectroscopic Method ◽  
Reaction Rates ◽  
Aliphatic Amines ◽  
Phenyl Isothiocyanate ◽  
Alkyl Aryl ◽  
Nucleophilic Addition Reaction ◽  
Kinetics Of ◽  
Aromatic And Aliphatic Amines

Kinetics of nucleophilic addition reaction of 9-isothiocyanatoacridine with seventeen aliphatic and aromatic amines in organic solvents has been studied by the VIS spectroscopic method. 9-Isothiocyanatoacridine reacted by about two orders of magnitude faster than phenyl isothiocyanate. The reaction rates of aliphatic amines were markedly affected by steric effects. Excepting 1-acridin-9-yl-3-butylthiourea (IIIo), the products obtained exhibited weaker fluorescence than the starting 9-isothiocyanatoacridine.

An acyl-Claisen approach to the synthesis of lignans and substituted pyrroles

2012 ◽  
Vol 84 (7) ◽  
pp. 1557-1565 ◽  
Author(s):  
David Barker ◽  
Benjamin Dickson ◽  
Nora Dittrich ◽  
Claire E. Rye
Keyword(s):  
Lewis Acid ◽  
Nucleophilic Addition ◽  
Claisen Rearrangement ◽  
Acid Catalyst ◽  
Protecting Groups ◽  
Organometallic Reagent ◽  
Wacker Oxidation ◽  
Lewis Acid Catalyst ◽  
Substituted Pyrroles

The acyl-Claisen rearrangement, also called a zwitterionic aza-Claisen rearrangement, allows for the synthesis of 2,3-syn-substituted morpholine pent-4-eneamides with high levels of diastereoselectivity. A wide variety of alkyl and aryl substituents can be introduced with yields highly dependent on the stoichiometry of the Lewis acid catalyst. The use of these morpholine amides in the synthesis of the tetrasubstituted tetrahydrofuran lignans fragransin A2, talaumidin, and galbelgin is summarized. The conversion of the Claisen-derived amides into aryl tetraline and 1,1-diarylbutanol lignans via alteration of the protecting groups is also described. Nucleophilic addition of an organometallic reagent to the morpholine amide followed by Wacker oxidation of the alkene gives highly substituted 1,4-diketones, which can be easily converted into fully substituted pyrroles.

Nucleophilic Addition Reaction of Aromatic Compounds with α-Chloroglycidates in the Presence of Lewis Acid.

ChemInform ◽  
2003 ◽  
Vol 34 (26) ◽  
Author(s):  
Jing-Rong Lin ◽  
Aidar T. Gubaidullin ◽  
Vakhid A. Mamedov ◽  
Sadao Tsuboi
Keyword(s):  
Lewis Acid ◽  
Aromatic Compounds ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Nucleophilic Addition Reaction

Nucleophilic Addition Reaction of Aromatic Compounds in the Presence of Lewis Acid

Synlett ◽  
2002 ◽  
Vol 2002 (06) ◽  
pp. 0899-0902 ◽  
Author(s):  
Jingrong Lin ◽  
Shu Kanazaki ◽  
Setsuo Kashino ◽  
Sadao Tsuboi
Keyword(s):  
Lewis Acid ◽  
Aromatic Compounds ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Nucleophilic Addition Reaction

ChemInform Abstract: Nucleophilic Addition Reaction of Aromatic Compounds in the Presence of Lewis Acid.

ChemInform ◽  
2010 ◽  
Vol 33 (37) ◽  
pp. no-no
Author(s):  
Jingrong Lin ◽  
Shu Kanazaki ◽  
Setsuo Kashino ◽  
Sadao Tsuboi
Keyword(s):  
Lewis Acid ◽  
Aromatic Compounds ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Nucleophilic Addition Reaction

Computationally-Guided Investigation of Dual Amine/pi Lewis Acid Catalysts for Direct Additions of Aldehydes and Ketones to Unactivated Alkenes and Alkynes

2020 ◽  
Author(s):  
Eric Greve ◽  
Jacob D. Porter ◽  
Chris Dockendorff
Keyword(s):  
Lewis Acid ◽  
Density Functional ◽  
Acid Catalyst ◽  
Metal Catalyst ◽  
Catalyst Poisoning ◽  
Lewis Acid Catalysts ◽  
Metal Ligands ◽  
Aldehydes And Ketones ◽  
Lewis Acid Catalyst ◽  
Catalyst Systems

Dual amine/pi Lewis acid catalyst systems have been reported for intramolecular direct additions of aldehydes/ketones to unactivated alkynes and occasionally alkenes, but related intermolecular reactions are rare and not presently of significant synthetic utility, likely due to undesired coordination of enamine intermediates to the metal catalyst. We reasoned that bulky metal ligands and bulky amine catalysts could minimize catalyst poisoning and could facilitate certain examples of direct intermolecular additions of aldehyde/ketones to alkenes/alkynes. Density Functional Theory (DFT) calculations were performed that suggested that PyBOX-Pt(II) catalysts for alkene/alkyne activation could be combined with MacMillan’s imidazolidinone organocatalyst for aldehyde/ketone activation to facilitate desirable C-C bond formations, and certain reactions were calculated to be more exergonic than catalyst poisoning pathways. As calculated, preformed enamines generated from the MacMillan imidazolidinone did not displace ethylene from a biscationic (<i>t</i>-Bu)PyBOX-Pt<sup>2+</sup>complex, but neither were the desired C-C bond formations observed under several different conditions.

Computationally-Guided Investigation of Dual Amine/pi Lewis Acid Catalysts for Direct Additions of Aldehydes and Ketones to Unactivated Alkenes and Alkynes

2020 ◽  
Author(s):  
Eric Greve ◽  
Jacob D. Porter ◽  
Chris Dockendorff
Keyword(s):  
Lewis Acid ◽  
Density Functional ◽  
Acid Catalyst ◽  
Metal Catalyst ◽  
Catalyst Poisoning ◽  
Lewis Acid Catalysts ◽  
Metal Ligands ◽  
Aldehydes And Ketones ◽  
Lewis Acid Catalyst ◽  
Catalyst Systems

Dual amine/pi Lewis acid catalyst systems have been reported for intramolecular direct additions of aldehydes/ketones to unactivated alkynes and occasionally alkenes, but related intermolecular reactions are rare and not presently of significant synthetic utility, likely due to undesired coordination of enamine intermediates to the metal catalyst. We reasoned that bulky metal ligands and bulky amine catalysts could minimize catalyst poisoning and could facilitate certain examples of direct intermolecular additions of aldehyde/ketones to alkenes/alkynes. Density Functional Theory (DFT) calculations were performed that suggested that PyBOX-Pt(II) catalysts for alkene/alkyne activation could be combined with MacMillan’s imidazolidinone organocatalyst for aldehyde/ketone activation to facilitate desirable C-C bond formations, and certain reactions were calculated to be more exergonic than catalyst poisoning pathways. As calculated, preformed enamines generated from the MacMillan imidazolidinone did not displace ethylene from a biscationic (<i>t</i>-Bu)PyBOX-Pt<sup>2+</sup>complex, but neither were the desired C-C bond formations observed under several different conditions.

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