Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids

2018 ◽  
Vol 83 (15) ◽  
pp. 7860-7866 ◽  
Author(s):  
Donghong Zhao ◽  
Haofan Luo ◽  
Binhui Chen ◽  
Wenteng Chen ◽  
Guolin Zhang ◽  
...  
Keyword(s):  
Exchange Reaction ◽  
Aromatic Acids ◽  
Aliphatic Acids ◽  
Palladium Catalyzed ◽  
Directing Group

The Direct Pd-Catalyzed β-C(sp3)–H Activation of Carboxylic Acids

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 1937-1943 ◽  
Author(s):  
Manuel van Gemmeren ◽  
Alexander Uttry
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Bond Activation ◽  
State Of The Art ◽  
Acid Moiety ◽  
Straightforward Manner ◽  
Aliphatic Acids ◽  
Tremendous Progress ◽  
Palladium Catalyzed ◽  
Directing Group

The carboxylic acid moiety is one of the most versatile and abundant functional groups. However, despite of tremendous progress in the field of C–H functionalization reactions its use as a directing group for C(sp3)–H activation has remained limited. In this Synpact article we present the challenges associated with the carboxylic acid moiety as a native directing group and report on the newest developments in this field, including our recent study in which we developed a generally applicable protocol for the direct palladium catalyzed β-C(sp3)–H arylation of propionic acid and related α-branched aliphatic acids giving access to hydrocinnamic acids derivatives in a highly straightforward manner.1 Introduction2 Challenges in the C(sp3)–H Bond Activation of Carboxylic Acids3 History/State of the Art4 Studies towards a General β-C(sp3)–H Functionalization of ­Aliphatic Acids5 Conclusion

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

The Antifungal Activity of Some Aliphatic and Aromatic Acids

1992 ◽  
Vol 57 (5) ◽  
pp. 1134-1142 ◽  
Author(s):  
Bohuslav Rittich ◽  
Marta Pirochtová ◽  
Jiří Hřib ◽  
Kamila Jurtíková ◽  
Petr Doležal
Keyword(s):  
Biological Activities ◽  
Pure Water ◽  
Water System ◽  
Penicillium Expansum ◽  
Aromatic Acids ◽  
Antifungal Activities ◽  
Aliphatic Acids ◽  
Significant Relationships ◽  
Physico Chemical ◽  
Connectivity Indices

The present paper deals with the relationship between biological activities of some aliphatic and aromatic acids and their physico-chemical parameters expressing the influence of hydrophobic factors. The test strain in the biotest of growth inhibition was the fungus Fusarium moniliforme CCMF-180 and Penicillium expansum CCMF-576. Significant relationship between antifungal activities of un-ionized form of aliphatic acids and their capacity factors (log k'0) extrapolated to pure water, partition coefficients determined in 1-octanol-water system (log Poct) and the first order of molecular connectivity indices (1χ) were calculated. The ionized form of aliphatic acids were antifungally active too. For benzoic acids significant relationships between antifungal activities and capacity factors of anionic form (log k'ia) were calculated.

Temporary (PO) directing group enabled carbazole ortho arylation via palladium catalysis

2021 ◽  
Vol 57 (16) ◽  
pp. 2021-2024
Author(s):  
Zhi-Chao Qi ◽  
Qin-Xin Lou ◽  
Yuan Niu ◽  
Shang-Dong Yang
Keyword(s):  
Palladium Catalysis ◽  
Palladium Catalyzed ◽  
Directing Group

An efficient palladium-catalyzed, temporary P(O) directing group assisted C–H bond arylation of carbazoles was achieved, accompanied by the directing group being self-shed spontaneously.

Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Synthesis ◽  
2021 ◽  
Author(s):  
Zheng-Yang Gu ◽  
Yang Wu ◽  
Feng Jin ◽  
Bao Xiaoguang ◽  
Ji-Bao Xia
Keyword(s):  
Carbon Monoxide ◽  
Palladium Catalysis ◽  
Computational Studies ◽  
Organic Azides ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
And Control

An atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

Palladium-catalyzed synthesis of aromatic acids from carbon monoxide and aromatic compounds via the aromatic CH bond activation

1990 ◽  
Vol 385 (2) ◽  
pp. 297-306 ◽  
Author(s):  
Tetsuro Jintoku ◽  
Yuzo Fujiwara ◽  
Itaru Kawata ◽  
Tomio Kawauchi ◽  
Hiroshi Taniguchi
Keyword(s):  
Carbon Monoxide ◽  
Aromatic Compounds ◽  
Bond Activation ◽  
Aromatic Acids ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium Catalyzed C-H Bond Acetoxylation: Isoxazolinyl as a Directing Group.

ChemInform ◽  
2016 ◽  
Vol 47 (44) ◽  
Author(s):  
Caiwei Geng ◽  
Minghui Jiang ◽  
Lifei Feng ◽  
Peng Jiao
Keyword(s):  
Palladium Catalyzed ◽  
Directing Group

ChemInform Abstract: One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling.

ChemInform ◽  
2016 ◽  
Vol 47 (32) ◽  
Author(s):  
Hongxiang Wu ◽  
Baiping Xu ◽  
Yue Li ◽  
Fengying Hong ◽  
Dezhao Zhu ◽  
...  
Keyword(s):  
Suzuki Coupling ◽  
Aromatic Acids ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed

scholarly journals Palladium-Catalyzed 2-(Neopentylsulfinyl)aniline Directed C-H Acetoxylation and Alkenylation of the Arylacetamides

2019 ◽  
Author(s):  
Maryia V. Barysevich ◽  
Marharyta V. Laktsevich-Iskryk ◽  
Anastasiya V. Krech ◽  
Vladimir N. Zhabinskii ◽  
Vladimir A. Khripach ◽  
...  
Keyword(s):  
One Pot ◽  
Palladium Catalyzed ◽  
Directing Group

A directing group that promotes very fast diacetoxylation of the arylacetamides is reported. The auxiliary also promotes alkenylation with vinyl ketones, which were generated in one-pot from the cyclopropanols.

scholarly journals Palladium-Catalyzed [3+2] Cycloaddition via Two-Fold 1,3-C(sp3)−H Activation

2020 ◽  
Author(s):  
Hojoon Park ◽  
jin-quan yu
Keyword(s):  
Functional Groups ◽  
Sulfonic Acid ◽  
Cycloaddition Reaction ◽  
Wide Range ◽  
Leaving Group ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
Overall Efficiency ◽  
Weak Coordination ◽  
Single Reaction

<div>Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) are required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3+2] reaction that utilizes C(sp<sup>3</sup>)–H activation to generate the three-carbon unit for formal cycloaddition with maleimides. We implemented a strategy where the initial C(sp<sup>3</sup>)–H activation/olefin insertion would trigger a relayed, second remote C(sp<sup>3</sup>)–H activation to complete a formal [3+2] cycloaddition. The diastereoselectivity profile of this reaction resembles that of a typical pericyclic cycloaddition reaction in that the relationships between multiple stereocenters are exquisitely controlled in a single reaction. The key to success was the use of weakly coordinating amides as the directing group, as undesired Heck or alkylation pathways were preferred with other types of directing groups. The use of the pyridine-3-sulfonic acid ligands is critical to enable C(sp<sup>3</sup>)–H activation directed by this weak coordination. The method is compatible with a wide range of amide substrates, including lactams, which lead to novel spiro-bicyclic products. The [3+2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity.</div>

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