Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air

Synlett ◽  
2021 ◽  
Author(s):  
Tran Quang Hung ◽  
Tuan Thanh Dang ◽  
Peter Langer ◽  
Ha Nam Do ◽  
Nguyen Minh Quan ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Coupling Reactions ◽  
Carbazole Derivatives ◽  
High Yields

AbstractAn efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

Latent Brønsted Base Solvent-Assisted Amide Formation from Amines and Acid Chlorides

Synthesis ◽  
2018 ◽  
Vol 50 (10) ◽  
pp. 2041-2057 ◽  
Author(s):  
Rikuto Otsuka ◽  
Kazuo Maruhashi ◽  
Tomohiko Ohwada
Keyword(s):  
Aromatic Amines ◽  
Benzoyl Chloride ◽  
Aliphatic Amines ◽  
Acid Chlorides ◽  
Amide Formation ◽  
Brønsted Base ◽  
High Yields

Weakly basic amines, including even neutral amines such as nitroaniline and aminocarboxylic acids, react with acid chlorides very efficiently in N,N-dimethylacetamide (DMAC), without addition of a base, to give the corresponding amides in high yields. The role of DMAC and related solvents as latent Brønsted bases was studied in these amidation reactions. Less basic amines, such as aromatic amines, reacted with benzoyl chloride faster than more basic aliphatic amines.

Reactions of Quinolizine- and Pyridino[1,2–a]pyrimidine-3-diazonium Tetrafluoroborates with Aliphatic Amines

2004 ◽  
Vol 59 (4) ◽  
pp. 380-385 ◽  
Author(s):  
Simon Rečnik ◽  
Jurij Svete ◽  
Branko Stanovnik
Keyword(s):  
Picolinic Acid ◽  
The Other ◽  
Aliphatic Amines ◽  
Secondary Amines ◽  
Primary Amines ◽  
Other Hand ◽  
High Yields

KeywordsReactions of 1-cyano-4-oxo-4H-quinolizine-3-diazonium tetrafluoroborate (1a) and 4-oxo-4Hpyridino[ 1,2-a]pyrimidine-3-diazonium tetrafluoroborate (1b) with aliphatic amines 2a - g were studied. Treatment of heteroaryldiazonium salts 1 with secondary amines 2a - d afforded the corresponding N-alkyl-N’-heteroaryltriazenes 3a - h in high yields. On the other hand, reactions of 1a with aliphatic primary amines 2e - g resulted in an unexpected rearrangements into the corresponding picolinic acid N-alkylcarboxamides 4a - c.

Efficient and Versatile Catalytic Systems for the N-Methylation of Primary Amines with Methanol Catalyzed by N-Heterocyclic Carbene Complexes of Iridium

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4617-4626 ◽  
Author(s):  
Ken-ichi Fujita ◽  
Genki Toyooka ◽  
Akiko Tuji
Keyword(s):  
Low Temperatures ◽  
Aromatic Amines ◽  
Catalytic Performance ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Iridium Complexes ◽  
Reaction Conditions ◽  
Catalytic Systems ◽  
Carbene Complexes ◽  
Amine Compounds

Efficient and versatile catalytic systems were developed for the N-methylation of both aliphatic and aromatic primary amines using methanol as the methylating agent. Iridium complexes bearing an N-heterocyclic carbene (NHC) ligand exhibited high catalytic performance for this type of transformation. For aliphatic amines, selective N,N-dimethylation was achieved at low temperatures (50–90 °C). For aromatic amines, selective N-monomethylation and selective N,N-dimethylation were accomplished by simply changing the reaction conditions (presence or absence of a base with an appropriate catalyst). These findings can be used to develop methods for synthesizing useful amine compounds having N-methyl or N,N-dimethyl moieties.

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.

Acceptorless amine dehydrogenation and transamination using Pd-doped layered double hydroxides

2018 ◽  
Author(s):  
Diana Ainembabazi ◽  
Nan An ◽  
Jinesh Manayil ◽  
Kare Wilson ◽  
Adam Lee ◽  
...  
Keyword(s):  
Layered Double Hydroxides ◽  
Oxidation States ◽  
Secondary Amines ◽  
Primary Amines ◽  
Acid Dissolution ◽  
Oxidative Amination ◽  
Strong Function ◽  
Excellent Activity ◽  
High Yields ◽  
Double Hydroxides

<div> <p>The synthesis, characterization, and activity of Pd-doped layered double hydroxides (Pd-LDHs) for for acceptorless amine dehydrogenation is reported. These multifunctional catalysts comprise Brønsted basic and Lewis acidic surface sites that stabilize Pd species in 0, 2+, and 4+ oxidation states. Pd speciation and corresponding cataytic performance is a strong function of metal loading. Excellent activity is observed for the oxidative transamination of primary amines and acceptorless dehydrogenation of secondary amines to secondary imines using a low Pd loading (0.5 mol%), without the need for oxidants. N-heterocycles, such as indoline, 1,2,3,4-tetrahydroquinoline, and piperidine, are dehydrogenated to the corresponding aromatics with high yields. The relative yields of secondary imines are proportional to the calculated free energy of reaction, while yields for oxidative amination correlate with the electrophilicity of primary imine intermediates. Reversible amine dehydrogenation and imine hydrogenation determine the relative imine:amine selectivity. Poisoning tests evidence that Pd-LDHs operate heterogeneously, with negligible metal leaching; catalysts can be regenerated by acid dissolution and re-precipitation.</p> </div> <br>

Addition of Aliphatic and Aromatic Amines to Catechol in Aqueous Solution Under Oxidizing Conditions

1989 ◽  
Vol 42 (3) ◽  
pp. 365 ◽  
Author(s):  
MK Manthey ◽  
SG Pyne ◽  
RJW Truscott
Keyword(s):  
Aqueous Solution ◽  
Aqueous Solutions ◽  
Aromatic Amines ◽  
Aliphatic Amines ◽  
Substitution Pattern ◽  
Vinylogous Amides ◽  
The Stability

The oxidation of catechol in the presence of two aliphatic and aromatic amines has been investigated. In aqueous solutions of pH 7.0 and 11.7, the substitution pattern of the adduct was dependent on the type of amine used. Aromatic amines produced 4,5-disubstituted o-quinones, whereas aliphatic amines gave either 2,4,5-trisubstituted or 2,4-disubstituted o-quinone adducts. A rationale based upon the stability of vinylogous amides is presented to account for the observed substitution pattern.

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

ChemInform Abstract: The “Benzostabase” Protecting Group for Primary Amines. Application to Aliphatic Amines.

ChemInform ◽  
2010 ◽  
Vol 23 (15) ◽  
pp. no-no
Author(s):  
R. P. BONAR-LAW ◽  
A. P. DAVIS ◽  
B. J. DORGAN ◽  
M. T. REETZ ◽  
A. WEHRSIG
Keyword(s):  
Aliphatic Amines ◽  
Primary Amines ◽  
Protecting Group

scholarly journals SYNTHESIS OF ESTERS OF HALOGENOACETIC ACIDS

2020 ◽  
Vol 2020 (3) ◽  
pp. 38-43
Keyword(s):  
Acetic Acid ◽  
Acid Catalyst ◽  
Primary Amines ◽  
Primary Alcohols ◽  
Sulfuric Acid Catalyst ◽  
Nucleophilic Exchange ◽  
Pmr Spectra ◽  
High Yields ◽  
Esterification Reactions ◽  
Acetic Acids

Amidoalkylating reagents containing a phthalimide group are used in the synthesis of hard-to-reach primary amines and complex heterocyclic compounds. These types of amidoalkylating compounds are suitable reagents for nucleophilic substituted reactions in acidic media due to their resistance to acids. Result of reactions of amidoalkylating reagents-N-hydroxyethylphthalimide and N-hydroxymethylphthalimide with aliphatic carbonic acids can also produce new bactericidal and fungicidal esters. In this study, halogen acids reacted with N-hydroxymethylphthalimide monochloric acetic acid, monobromic acetic acid, monoiodic acetic acid, trifluoric acetic acid and trichloroacetic acid, as well as, N-b-hydroxyethylphthaleidyl monohydric acid. As a result of the reactions, new phthalimidomethyl and phthalimidoethyl esters of haloacetic acids were synthesized. The physical properties of crystalline esters have been determined. The structure of these compounds were confirmed by the analysis of their IR and PMR spectra. The esterification reactions of halogenated acetic acids were carried out in a benzene solvent and a sulfuric acid catalyst with primary alcohols, N-hydroxymethylphthalimide and N-β- beta hydroxyethylphthalimide,. It was found that in a benzene solvent, which increases the rate of bimolecular nucleophilic exchange in primary alcohols, phthalimidoethyl esters of halogen acid are formed in high yields, and phthalimidomethyl esters are formed in low yields. It was shown that the reaction of esterification of halogen acids with N-hydroxymethylphthalimide proceeds with monomolecular nucleophilic exchange.

Sign in / Sign up

Export Citation Format

Share Document