Copper-Catalyzed Decarboxylative N-Arylation of Indole-2-carboxylic Acids

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1803-1808 ◽  
Author(s):  
Yan Zhang ◽  
Zhe-Yao Hu ◽  
Xin-Chang Li ◽  
Xun-Xiang Guo
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Aryl Halides ◽  
Synthetic Method ◽  
Alternative Route ◽  
Reaction Proceeds ◽  
High Yields

A novel decarboxylative N-arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu2O as the catalyst to give the corresponding N-aryl indoles in high yields. This synthetic method shows good functional group tolerance and offers an alternative route to construct N-aryl indoles.

7,10-Dibromo-2,3-dicyanopyrazinophenanthrene Aggregates as a Photosensitizer for Nickel-Catalyzed Aryl Esterification

Synlett ◽  
2021 ◽  
Author(s):  
Xiaoqiang Yu ◽  
Min He ◽  
Shilei Yang ◽  
Ming Bao
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Bond Formation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Ni Catalyst ◽  
Coupling Reactions ◽  
Formation Reaction ◽  
Cross Coupling Reactions ◽  
Reaction Proceeds

AbstractSelf-assembled aggregates of 7,10-dibromo-2,3-dicyanopyrazinophenanthrene which act as a new organophotocatalyst in combination with Ni catalyst for the Caryl–Oacyl cross-coupling reactions of carboxylic acids with aryl halides are described. This visible-light-induced Caryl–Oacyl bond-formation reaction proceeds smoothly to afford aryl esters with satisfactory to excellent yields.

Copper(II)-Catalyzed C–N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol

Synlett ◽  
2019 ◽  
Vol 30 (19) ◽  
pp. 2161-2168
Author(s):  
Fangyu Du ◽  
Qifan Zhou ◽  
Yang Fu ◽  
Yuanguang Chen ◽  
Ying Wu ◽  
...  
Keyword(s):  
Diethylene Glycol ◽  
Functional Group ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Mild Conditions ◽  
Natural Ligand ◽  
Highly Effective ◽  
High Yields

Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C–N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.

Highly Efficient Copper-Catalyzed Dehydrogenative Cross-Coupling of Azoles and α-Amino Carbonyl Compounds

Synthesis ◽  
2020 ◽  
Author(s):  
Jiu-Jian Ji ◽  
Zhi-Qiang Zhu ◽  
Zong-Bo Xie ◽  
Juan Tang ◽  
En Yuan ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Functional Group ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthetic Method ◽  
Diverse Range ◽  
Highly Efficient ◽  
Cross Coupling Reaction ◽  
Butyl Peroxide ◽  
High Yields

A novel and highly efficient dehydrogenative cross-coupling reaction between α-amino carbonyl compounds and azoles by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant was described. A diverse range of azoles underwent the dehydrogenative imidoylation smoothly with various α-amino carbonyl compounds for the exclusive formation of the corresponding N-imidoyl azoles in high yields under air. The synthetic method has the advantages of good functional-group tolerance, wide substrate scope, excellent yields and simple operation, thus providing a convenient and practical protocol for the synthesis of various functionalized azoles.

scholarly journals Triflic Anhydride Promoted Synthesis of Primary Amides and their Conversion into Nitriles

SynOpen ◽  
2018 ◽  
Vol 02 (02) ◽  
pp. 0180-0191
Author(s):  
Anil Rana ◽  
Varun Kumar ◽  
Lata Tiwari ◽  
Anamika Thakur ◽  
Chhuttan Meena ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Reaction Conditions ◽  
One Pot ◽  
Limited Success ◽  
High Yields

A facile, two-pot conversion of carboxylic acids into the corresponding nitriles has been developed using triflic anhydride as a promoter and aqueous NH4OH as a source of nitrogen. The methodology involves synthesis of primary amides from carboxylic acids as the key first step using triflic anhydride and aqueous NH4OH as a source of ­nitrogen. Triflic anhydride is also found to be an excellent reagent for conversion of primary amides into nitriles, affording high yields with considerable chemoselectivity and functional group tolerance. In spite of the mild reaction conditions and broad substrate scope for the two-step conversions, all attempts for one-pot domino conversion of acids into nitriles exhibited limited success because of poor yields.

Ruthenium(II)-Catalyzed C–H Alkynylation of Heterocycles under Chelation Assistance

Synlett ◽  
2017 ◽  
Vol 29 (05) ◽  
pp. 658-662 ◽  
Author(s):  
Congjun Liu ◽  
Yanping Liu ◽  
Feng Chang ◽  
Qiaojuan Jiang ◽  
Zhiwei Ma
Keyword(s):  
Functional Group ◽  
Hypervalent Iodine ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
High Yields

An efficient ruthenium(II)-catalyzed, chelation-assisted C–H alkynylation of heterocycles is described using hypervalent iodine–alkyne as an alkynylating reagent. This reaction proceeds smoothly under mild conditions with high regioselectivity and good functional group tolerance, delivering the desired alkynylated indoles, thiophene, furan, and pyrrole in high yields.

Construction of Esters through Sulfuryl Fluoride (SO2F2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature

Synthesis ◽  
2019 ◽  
Vol 51 (20) ◽  
pp. 3901-3907 ◽  
Author(s):  
Shi-Meng Wang ◽  
Njud S. Alharbi ◽  
Hua-Li Qin
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Functional Group ◽  
High Efficiency ◽  
Sulfuryl Fluoride ◽  
Mild Conditions ◽  
High Yields

A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO2F2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.

Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane

Synlett ◽  
2021 ◽  
Author(s):  
Yongjun Mao ◽  
Shi-Liang Shi ◽  
Shichao Wei
Keyword(s):  
Functional Group ◽  
Aryl Halides ◽  
Aryl Bromides ◽  
Ligand Free ◽  
Styrene Derivatives ◽  
High Yields

AbstractWe herein disclose the first Ni-catalyzed Hiyama coupling of aryl halides with vinylsilanes. This protocol uses cheap, nontoxic, and stable vinyltrimethoxysilane as the vinyl donor, proceeds under mild and ligand-free conditions, furnishing a diverse variety of styrene derivatives in high yields with excellent functional group compatibility.

Catalytic Enantioselective Benzylation Directly from Aryl Acetic Acids

2018 ◽  
Author(s):  
Patrick Moon ◽  
Zhongyu Wie ◽  
Rylan Lundgren
Keyword(s):  
Functional Group ◽  
Terminal Event ◽  
Radical Intermediates ◽  
Carbon Carbon Bond ◽  
Or Groups ◽  
Reaction Proceeds ◽  
Wide Availability ◽  
Metal Catalyzed ◽  
The Stability ◽  
Acetic Acids

The stability and wide availability of carboxylic acids make them valuable reagents in chemical synthesis. Most transition metal catalyzed processes using carboxylic acid substrates are initiated by a decarboxylation event that generates reactive carbanion or radical intermediates. Developing enantioselective methodologies relying on these principles can be challenging, as highly reactive species tend to react indiscriminately without selectivity. Furthermore, anionic or radical intermediates generated from decarboxylation can be incompatible with protic and electrophilic functionality, or groups that undergo trapping with radicals. We demonstrate that metal-catalyzed enantioselective benzylation reactions of allylic electrophiles can occur directly from aryl acetic acids. The reaction proceeds via a pathway in which decarboxylation is the terminal event, occurring after stereoselective carbon–carbon bond formation. The mechanistic features of the process enable enantioselective benzylation without the generation of a highly basic nucleophile. Thus, the process has broad functional group compatibility that would not be possible employing established protocols.<br>

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.

Efficient CDI/CH3SO3H -Catalyzed, Microwave-Assisted Synthesis of 2-Substituted Benzothiazoles

2018 ◽  
Vol 16 (1) ◽  
pp. 34-39
Author(s):  
Yao-Wei Li ◽  
Pei-Ming Zhang ◽  
Rui Li ◽  
Yan Bai ◽  
Yu Yu ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Carboxylic Acids ◽  
1H Nmr ◽  
Good Yield ◽  
Microwave Assisted Synthesis ◽  
Synthetic Method ◽  
Benzothiazole Derivatives ◽  
Microwave Assisted ◽  
Highly Effective

CDI combined with CH3SO3H was found to be highly effective for the cyclization of 2-aminothiophenol derivatives with carboxylic acids under MW condition. Fourteen benzothiazole derivatives were synthesized in good yield and their structures were characterized by 1H-NMR, 13CNMR, IR and mass spectrometry. This simple, rapid synthetic method is believed to provide a useful process for the synthesis of 2-substituted benzothiazole compounds.

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