Chemoselectivity in Esterification Reactions – Size Matters after All

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3460-3470 ◽  
Author(s):  
Julian Helberg ◽  
Marta Marin-Luna ◽  
Hendrik Zipse
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Temperature Effects ◽  
Aliphatic Acid ◽  
Secondary Alcohols ◽  
Acid Chlorides ◽  
Aromatic Carboxylic Acids ◽  
Esterification Reactions

The reaction of carboxylic acid chlorides with secondary alcohols carrying either flexible alkyl or rigid aryl substituents was studied through a series of competition experiments. Aliphatic acid chlorides react preferentially with the aryl-substituted alcohols, while acid chlorides derived from aromatic carboxylic acids react with very low selectivity. Catalysis by 9-azajulolidine (TCAP) increases the selectivity strongly, while solvent and temperature effects are only moderate. The size of the alcohol substituents seems to impact selectivities only for rigid aryl substituents, and highest selectivities have been found for 1-(1-pyrenyl)ethanol.

scholarly journals Efficient one-pot, four-component synthesis of N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives from the reaction of (isocyanoimino)triphenylphosphorane, dibenzylamine, an aromatic carboxylic acid and cyclobutanone

2012 ◽  
Vol 77 (9) ◽  
pp. 1175-1180 ◽  
Author(s):  
Nahid Shajari ◽  
Reza Kazemizadeh ◽  
Ali Ramazani
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Aromatic Carboxylic Acid ◽  
One Pot ◽  
Aromatic Carboxylic Acids ◽  
High Yields ◽  
Neutral Conditions

Four-component reaction of cyclobutanone, dibenzylamine and (Nisocyanimino) triphenylphosphorane in the presence of aromatic carboxylic acids proceed smoothly at room temperature and under neutral conditions to afford N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives in high yields.

ChemInform Abstract: A New Synthesis of β,γ-Alkenyl Carboxylic Acids from α,β-Alkenyl Carboxylic Acid Chlorides and α,β-Alkenyl Aldehydes with One-Carbon Elongation.

ChemInform ◽  
2010 ◽  
Vol 33 (12) ◽  
pp. no-no
Author(s):  
Tsuyoshi Satoh ◽  
Akira Nakamura ◽  
Atsuko Iriuchijima ◽  
Yasumasa Hayashi ◽  
Ko-ichi Kubota
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Acid Chlorides ◽  
New Synthesis

Rh(III)-Catalyzed Decarboxylativeortho-Heteroarylation of Aromatic Carboxylic Acids by Using the Carboxylic Acid as a Traceless Directing Group

2015 ◽  
Vol 17 (7) ◽  
pp. 1762-1765 ◽  
Author(s):  
Xurong Qin ◽  
Denan Sun ◽  
Qiulin You ◽  
Yangyang Cheng ◽  
Jingbo Lan ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Aromatic Carboxylic Acids ◽  
Directing Group

scholarly journals Formamide catalyzed activation of carboxylic acids – versatile and cost-efficient amidation and esterification

2019 ◽  
Vol 10 (31) ◽  
pp. 7399-7406 ◽  
Author(s):  
Peter H. Huy ◽  
Christelle Mbouhom
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Bond Formation ◽  
Acid Chlorides ◽  
Cost Efficient

Formamide catalysis enables highly cost-efficient amide C–N and ester C–O bond formation through carboxylic acid chlorides as essential intermediates.

Organocatalytic Electrochemical C–H Lactonization of Aromatic Carboxylic Acids

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2924-2929 ◽  
Author(s):  
Sanzhong Luo ◽  
Longji Li ◽  
Qi Yang ◽  
Zongbin Jia
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Glassy Carbon ◽  
Bond Formation ◽  
Carbon Electrodes ◽  
Glassy Carbon Electrodes ◽  
Aromatic Carboxylic Acids ◽  
Radical Substitution ◽  
Carboxyl Radical ◽  
Oxygen Bond

An electrochemical strategy has been developed for radical arene carbon–oxygen bond formation. This reaction utilizes DDQ as a redox mediator, with inexpensive glassy carbon electrodes to facilitate an intramolecular lactonization of biphenyl-2-carboxylic acid derivatives via aromatic carboxyl radical substitution to give 6H-benzo[c]chromen-6-ones.

scholarly journals Synthesis and Screening of Substituted Thiadiazoles Against Gleophyllum Straitum

2004 ◽  
Vol 1 (3) ◽  
pp. 184-188
Author(s):  
M. G. H. Zaidi ◽  
Seema Zaidi ◽  
I. P. Pandey
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Wood Preservation ◽  
Acid Chlorides

Cyclocondensation of a series of substituted phenoxy methylene carboxylic acids with thiosemoicarbazides afforded 2-Amino-5-Aryloxy Methylene –1,3,4 Thiadiazoles (Ia-Ie). The later were subsequently condensed with different phenoxymethylene carboxylic acid chlorides into 2- Aryloxy Methyleneamido-5-Aryloxy Methylene–1,3,4-Thiadiazoloyl Amides. The wood preservation efficiency of the both class of compounds was evaluated against a wood rotting fungusGleophyllum Straitumat different concentrations using food poison technique. In general phenoxy derivatives have shown more control over the growth ofGleophyllum Straitumthan their corresponding aminothiadiazoles at 500 ppm. The chlorophenoxy-substituted thiadiazoles among all have shown more activity then others againstGleophyllum Straitum.

A new synthesis of β,γ-alkenyl carboxylic acids from α,β-alkenyl carboxylic acid chlorides and α,β-alkenyl aldehydes with one-carbon elongation

Tetrahedron ◽  
2001 ◽  
Vol 57 (48) ◽  
pp. 9689-9696 ◽  
Author(s):  
Tsuyoshi Satoh ◽  
Akira Nakamura ◽  
Atsuko Iriuchijima ◽  
Yasumasa Hayashi ◽  
Ko-ichi Kubota
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Acid Chlorides ◽  
New Synthesis

Reactions of Some Pyrazole-3-Carboxylic Acids and Carboxylic Acid Chlorides with Various O- and N- Nucleophiles

2013 ◽  
Vol 10 (8) ◽  
pp. 602-610 ◽  
Author(s):  
Ilhan Ilhan ◽  
Ayse Caglayan ◽  
Zulbiye Onal ◽  
Senem Akkoc ◽  
Mehmet Cadır
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Acid Chlorides

Study on solubilization of telmisartan by forming cocrystal with aromatic carboxylic acid

CrystEngComm ◽  
2021 ◽  
Author(s):  
Guojia Yu ◽  
Xinjian Chen ◽  
Lichao He ◽  
Xiangrong Li ◽  
Zhiyong Zhou ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Aromatic Carboxylic Acid ◽  
Aromatic Carboxylic Acids

The solubility of insoluble telmisartan (TEL) was improved by forming new cocrystal forms with several aromatic carboxylic acids. All solid forms showed three dissolution modes: TEL-HBA achieved maximum release equilibrium...

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