Direct C-3 alkylation of coumarins via decarboxylative coupling with carboxylic acids

2019 ◽  
Vol 43 (24) ◽  
pp. 9328-9332 ◽  
Author(s):  
Farnaz Jafarpour ◽  
Masoumeh Darvishmolla ◽  
Narges Azaddoost ◽  
Farid Mohaghegh
Keyword(s):  
Carboxylic Acids ◽  
Aqueous Media ◽  
Metal Free ◽  
Decarboxylative Coupling

A metal-free direct alkylation of coumarins using carboxylic acids in aqueous media with a broad substrate scope is devised.

Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 363-368 ◽  
Author(s):  
Can Jin ◽  
Bin Sun ◽  
Tengwei Xu ◽  
Liang Zhang ◽  
Rui Zhu ◽  
...  
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Regioselective Alkylation ◽  
Decarboxylative Coupling ◽  
Aliphatic Carboxylic Acids

A visible-light-induced direct C–H alkylation of imidazo[1,2-a]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N-hydroxyphthalimide (NHP) esters as alkylation reagents. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) were tolerated in this protocol, giving the corresponding C-5-alkylated products in moderate to excellent yields. Mechanistic studies indicate that a radical decarboxylative coupling pathway was involved in this process.

Metal free decarboxylative aminoxylation of carboxylic acids using a biphasic solvent system

2021 ◽  
Vol 19 (1) ◽  
pp. 273-278
Author(s):  
Göran Schulz ◽  
Andreas Kirschning
Keyword(s):  
Carboxylic Acids ◽  
Solvent System ◽  
Radical Scavenger ◽  
Synthetic Approach ◽  
Metal Free ◽  
System P

The oxidative radical decarboxylation of carboxylic acids with TEMPO as radical scavenger in a biphasic solvent system is reported which is successfully used in a new synthetic approach for the antidepressants indatraline.

Dissociation of imino proton(s) of a highly water-soluble metal-free phthalocyanine and determination of its pKa value in water

2013 ◽  
Vol 17 (06n07) ◽  
pp. 447-453 ◽  
Author(s):  
Hiroaki Isago ◽  
Harumi Fujita
Keyword(s):  
Aqueous Media ◽  
Thermal Reaction ◽  
Water Soluble ◽  
Acid Dissociation ◽  
Acid Dissociation Constant ◽  
Metal Free ◽  
Imino Proton ◽  
Pka Value ◽  
Triton X

Dissociation of imino proton(s) in the cavity of the macrocycle of a highly water-soluble, metal-free phthalocyanine ( H 2( H 4 tsppc ); where H 4 tsppc denotes tetrakis{(2′,6′-dimethyl-4′-sulfonic acid)phenoxy}phthalocyaninate) in ethanolic and aqueous solutions has spectrophotometrically been investigated. The spectral changes associated with reaction with NaOH have been found to involve one-proton transfer process in aqueous media while two-protons process in ethanolic media. The acid-dissociation constant of the first imino proton in water (in the presence of Triton X-100) has been determined to be 12.5 ± 0.2 (as pKa) at 25 °C. The doubly deprotonated species in EtOH has been easily converted to its corresponding cobalt(II) derivative by thermal reaction with anhydrous CoCl 2.

Oxidation of α-Substituted Carbonyl Compounds to Carboxylic Acids in Aqueous Media Using Ultrasound

1997 ◽  
Vol 27 (9) ◽  
pp. 1601-1605 ◽  
Author(s):  
D. T. C. Yang ◽  
C. J. Zhang ◽  
P. P. Fu ◽  
G. W. Kabalka
Keyword(s):  
Carboxylic Acids ◽  
Carbonyl Compounds ◽  
Aqueous Media

Cationic Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carboxylic acids in aqueous media

2018 ◽  
Vol 59 (13) ◽  
pp. 1192-1195 ◽  
Author(s):  
Yuxin Ni ◽  
Kaixuan Song ◽  
Kai Shen ◽  
Zhenyu Yang ◽  
Rui Liu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Aqueous Media ◽  
Conjugate Addition ◽  
Arylboronic Acids ◽  
Unsaturated Carboxylic Acids

Palladium-catalyzed decarboxylative coupling reaction with alkynyl carboxylic acids and arylsiloxanes

2016 ◽  
Vol 57 (41) ◽  
pp. 4581-4584 ◽  
Author(s):  
Jisun Jang ◽  
Gabriel Charles Edwin Raja ◽  
Ju-Hyeon Lee ◽  
Yujeong Son ◽  
Jimin Kim ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Coupling Reaction ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed
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