Aliphatic Sulfonyl Fluoride Synthesis via Reductive Decarboxylative Fluorosulfonylation of Aliphatic Carboxylic Acids NHPI Esters

2022 ◽  
Author(s):  
Zhanhu Ma ◽  
Yongan Liu ◽  
Xiaoyu Ma ◽  
Xiaojun Hu ◽  
Yong Guo ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Sulfur Dioxide ◽  
Carboxylic Acids ◽  
Efficient Method ◽  
Aliphatic Carboxylic Acids ◽  
Sulfonyl Fluoride

Based on radical sulfur dioxide insertion and fluorination strategy, we have developed an efficient method for aliphatic sulfonyl fluoride synthesis from abundant carboxylic acid, reductant, sulfur dioxide surrogate and electrophilic...

Direct C(sp3)–H Activation of Carboxylic Acids

Synthesis ◽  
2019 ◽  
Vol 52 (04) ◽  
pp. 479-488 ◽  
Author(s):  
Alexander Uttry ◽  
Manuel van Gemmeren
Keyword(s):  
Carboxylic Acid ◽  
General Solution ◽  
Carboxylic Acids ◽  
Bond Activation ◽  
Acid Moiety ◽  
Group Approach ◽  
Research Fields ◽  
Directing Group ◽  
Aliphatic Carboxylic Acids

Carboxylic acids are important in a variety of research fields and applications. As a result, substantial efforts have been directed towards the C–H functionalization of such compounds. While the use of the carboxylic acid moiety as a native directing group for C(sp2)–H functionalization reactions is well established, as yet there is no general solution for the C(sp3)–H activation of aliphatic carboxylic acids and most endeavors have instead relied on the introduction of stronger directing groups. Recently however, novel ligands, tools, and strategies have emerged, which enable the use of free aliphatic carboxylic acids in C–H-activation-based transformations.1 Introduction2 Challenges in the C(sp3)–H Bond Activation of Carboxylic Acids3 The Lactonization of Aliphatic Carboxylic Acids4 The Directing Group Approach5 The Direct C–H Arylation of Aliphatic Carboxylic Acids6 The Direct C–H Olefination of Aliphatic Carboxylic Acids7 The Direct C–H Acetoxylation of Aliphatic Carboxylic Acids8 Summary

ALIPHATIC CARBOXYLIC ACIDS IN CHERNOZEMIC SOILS

1982 ◽  
Vol 62 (3) ◽  
pp. 487-494 ◽  
Author(s):  
J. F. Dormaar
Keyword(s):  
Organic Matter ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Dioctyl Phthalate ◽  
Gas Chromatography Mass Spectrometry ◽  
Grass Species ◽  
Aliphatic Carboxylic Acid ◽  
High Resolution Gas Chromatography ◽  
Aliphatic Carboxylic Acids ◽  
Extractable Organic Matter

For Chernozemic soils, published information on the aliphatic carboxylic acid fraction of the organic matter is scarce. Yet, geologically they are chemically stable and persist for long periods of time. The distribution of chloroform/methanol-extractable aliphatic carboxylic acids in five uncultivated and three cultivated Chernozemic soils and the roots of four grass species was, therefore, determined. Twenty-three organic acids (up to C30) were tentatively identified by high resolution gas chromatography-mass spectrometry. Hexanedioic acid and dioctyl phthalate were suspected of being contaminants. The relative proportions of aliphatic carboxylic acids varied for different soils. Tree invasions, overgrazing, and cultivation decreased the total aliphatic carboxylic acid content at the expense of the lower weight aliphatic carboxylic acids. Since the aliphatic carboxylic acids formed only a small portion of the total solvent-extractable organic matter and decreased after cultivation, the results do not explain the observation reported earlier that solvent-extractable organic matter of Chernozemic soils increased as a result of cultivation.

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds

2018 ◽  
Author(s):  
Erin Stache ◽  
Alyssa B. Ertel ◽  
Tomislav Rovis ◽  
Abigail G. Doyle
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Single Step ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Synthetic Strategy ◽  
Acyl Radicals ◽  
Benzyl Radicals ◽  
Aliphatic Carboxylic Acids

Alcohols and carboxylic acids are ubiquitous functional groups found in organic molecules that could serve as radical precursors, but C–O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen centered nucleophile. We first show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H-atom trapping to afford the deoxygenated product. Using the same method, we demonstrate access to synthetically versatile acyl radicals which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge new C–O, C–N and C–C bonds in a single step.

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

scholarly journals Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids

2021 ◽  
pp. 174751982098715
Author(s):  
Khethobole C Sekgota ◽  
Michelle Isaacs ◽  
Heinrich C Hoppe ◽  
Ronnett Seldon ◽  
Digby F Warner ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Coupling Agent ◽  
Methyl Esters ◽  
Acid Anhydride

Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.

Improved QSAR Analysis of the Toxicity of Aliphatic Carboxylic Acids

2003 ◽  
Vol 73 (11) ◽  
pp. 1792-1798 ◽  
Author(s):  
F. P. Maguna ◽  
M. B. Ninez ◽  
N. B. Okulik ◽  
E. A. Castro
Keyword(s):  
Carboxylic Acids ◽  
Qsar Analysis ◽  
Aliphatic Carboxylic Acids

Radical addition to acrylonitrile via catalytic photochemical decarboxylation of aliphatic carboxylic acids

2013 ◽  
Vol 54 (32) ◽  
pp. 4324-4326 ◽  
Author(s):  
Yasuharu Yoshimi ◽  
Sonoka Washida ◽  
Yoshiki Okita ◽  
Keisuke Nishikawa ◽  
Kousuke Maeda ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Radical Addition ◽  
Aliphatic Carboxylic Acids
Sign in / Sign up

Export Citation Format

Share Document