Aryl Alkynyl Carboxylic Acids Research Articles

Nickel-catalyzed oxidative decarboxylative coupling reactions between alkynyl carboxylic acids and arylboronic acids

Nickel-catalyzed decarboxylative coupling reactions between aryl alkynyl carboxylic acids and arylboronic acids were developed. When aryl alkynyl carboxylic acids were reacted with arylboronic acids in the presence of NiCl2 (10mol%), 2,2′-bipyridine (20mol%), Na2CO3 (1.0equiv), and Ag2CO3 (1.0equiv) in DMF at 80°C for 18h, the corresponding diaryl alkynes products were formed in moderate to good yields.

ChemInform Abstract: Copper‐Catalyzed Decarboxylative Hydroboration: Synthesis of Vinyl Boronic Esters

Abstractstarting from aryl alkynyl carboxylic acids and bis(pinacolato)diboron with good functional group tolerance

Transition‐Metal‐Free Decarboxylative Coupling Reactions for the Synthesis of Propargyl Alcohols

AbstractPropargyl alcohols have been directly synthesized by decarboxylative coupling reactions with an alkynyl carboxylic acid and an aldehyde/ketone in the absence of a transition‐metal catalyst. When the decarboxylative coupling reaction was conducted with Cs2CO3 in DMSO, the desired propargyl alcohols were formed in good yield. In addition, the reactions with 2,2,2‐trifluoroacetophenone and aryl alkynyl carboxylic acids gave trifluoromethylated propargyl alcohols.

Copper‐catalyzed Decarboxylative Hydroboration: Synthesis of Vinyl Boronic Esters

Vinyl boronic esters were synthesized from aryl alkynyl carboxylic acids and bis(pinacolato)diboron using a copper‐catalyzed decarboxylative reaction. The reaction was conducted with CuI (10 mol%), bis‐[2‐(diphenylphosphino)phenyl]ether(20 mol%), and LiOMe (20 mol%) in DMSO at 50 °C for 16 h. This method provided the desired vinyl boronic esters in good‐to‐moderate yields and showed good functional group tolerance.

ChemInform Abstract: Pd‐Catalyzed Decarboxylative Coupling of Arylalkynyl Carboxylic Acids with Allyl Ethers: Regioselective Synthesis of Branched 1,3‐Enynes.

AbstractThe title reaction with a variety of non‐activated allylic ethers as coupling partners proceeds under mild conditions at 30°C whereas allylic thioethers require 80°C as reaction temperature.

ChemInform Abstract: Copper‐Catalyzed Synthesis of Amino‐Substituted Polycyclic Aromatic Hydrocarbons by the Sequential Reaction Between Aryl Alkynyl Carboxylic Acids and Amines.

ChemInformVolume 47, Issue 4 Preparative Organic Chemistry ChemInform Abstract: Copper-Catalyzed Synthesis of Amino-Substituted Polycyclic Aromatic Hydrocarbons by the Sequential Reaction Between Aryl Alkynyl Carboxylic Acids and Amines. Jinseop Choi, Jinseop Choi Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this authorKyungho Park, Kyungho Park Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this authorJeongah Lim, Jeongah Lim Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this authorHyun Min Jung, Hyun Min Jung Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this authorSunwoo Lee, Sunwoo Lee Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this author Jinseop Choi, Jinseop Choi Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this authorKyungho Park, Kyungho Park Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this authorJeongah Lim, Jeongah Lim Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this authorHyun Min Jung, Hyun Min Jung Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this authorSunwoo Lee, Sunwoo Lee Dep. Appl. Chem., Kumoh Natl. Inst. Technol., Gumi 730-701, S. KoreaSearch for more papers by this author First published: 07 January 2016 https://doi.org/10.1002/chin.201604024Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume47, Issue4January, 2016 RelatedInformation

Pd-catalyzed decarboxylative coupling of arylalkynyl carboxylic acids with allyl ethers: regioselective synthesis of branched 1,3-enynes

This work reported an efficient and novel method to prepare branched 1,3-enynes via Pd(II)-catalyzed decarboxylative coupling of arylalkynyl carboxylic acids with allylic ethers under mild conditions. Various arylalkynyl carboxylic acids and allylic ethers could participate in the reaction, regioselectively affording the desired branched 1,3-enynes in moderate to good yields.

Copper‐Catalyzed Synthesis of Amino‐Substituted Polycyclic Aromatic Hydrocarbons by the Sequential Reaction between Aryl Alkynyl Carboxylic Acids and Amines

AbstractAmino‐substituted polycyclic aromatic hydrocarbons were obtained by the reaction between aryl alkynyl carboxylic acids and amines in the presence of a copper catalyst. The hydrocarbons were obtained in good yield without the need to isolate the 1,4‐diaryl‐1,3‐butadiyne intermediate. The best result was obtained using a combination of CuCl and Cu(OTf)2, and the reactions of cyclic and acyclic secondary amines afforded the desired products.

ChemInform Abstract: Palladium‐Catalyzed Decarboxylative Trifluoroethylation of Aryl Alkynyl Carboxylic Acids.

A trifluoroethylation of alkynes through a palladium-catalyzed decarboxylative coupling reaction was developed. When alkynyl carboxylic acids and ICH2CF3 were allowed to react with [Pd(η3-allyl)Cl]2/XantPhos and Cs2CO3 in N,N-dimethylformamide (DMF) at 80 °C for 1 h, the desired products were formed in good yields. This catalytic system showed high functional group tolerance.

Copper‐Catalyzed Selective Synthesis of Isoindolin‐1‐ones and Isoquinolin‐1‐ones from the Three‐Component Coupling of 2‐Halobenzoic Acid, Alkynylcarboxylic Acid and Ammonium Acetate

AbstractIsoindolin‐1‐ones and isoquinolin‐1‐ones were selectively synthesized from the reaction of 2‐halobenzoic acid, arylalkynylcarboxylic acid and ammonium acetate (NH4OAc) in the presence of cesium carbonate (Cs2CO3) and a copper catalyst. Conducting the reaction under one‐pot conditions provided isoindolin‐1‐ones in good yields. Changing the addition sequence of ammonium acetate after all reagents had reacted at 120 °C for 6 h selectively produced isoquinolin‐1‐ones. A variety of arylalkynylcarboxylic acids produced the corresponding isoindolin‐1‐ones and isoquinolin‐1‐ones in good yields.magnified image

Copper-catalyzed decarboxylative coupling reactions for the synthesis of propargyl amines

When aryl alkynyl carboxylic acids were allowed to react with amines and aldehydes in CH3CN at 80°C in the presence of 10mol% CuI, the desired propargyl amines were formed in good yields. This coupling reaction demonstrated to work across a broad range of reagents including functionalized aryl alkynyl carboxylic acids, aliphatic and aromatic aldehydes, and cyclic and acyclic amines.

Palladium-Catalyzed Decarboxylative Trifluoroethylation of Aryl Alkynyl Carboxylic Acids

A trifluoroethylation of alkynes through a palladium-catalyzed decarboxylative coupling reaction was developed. When alkynyl carboxylic acids and ICH2CF3 were allowed to react with [Pd(η(3)-allyl)Cl]2/XantPhos and Cs2CO3 in N,N-dimethylformamide (DMF) at 80 °C for 1 h, the desired products were formed in good yields. This catalytic system showed high functional group tolerance.

ChemInform Abstract: Ligand‐Free Palladium‐Catalyzed Decarboxylative Coupling Reactions of Aryl Iodides and Alkynyl Carboxylic Acids.

Abstract Pd-CNT nanocomposite was prepared from the composite of thiolated MWNT and Na 2 PdCl 4 . The palladium nanoparticles possess an average diameter of 2.9 nm with a narrow size distribution for the Pd-CNT. This Pd-CNT showed good activities in the coupling reactions of aryl iodides and aryl alkynyl carboxylic acids to produce the diaryl alkynes in good yields without any additional ligand.

Ligand-free palladium-catalyzed decarboxylative coupling reactions of aryl iodides and alkynyl carboxylic acids

Pd-CNT nanocomposite was prepared from the composite of thiolated MWNT and Na2PdCl4. The palladium nanoparticles possess an average diameter of 2.9 nm with a narrow size distribution for the Pd-CNT. This Pd-CNT showed good activities in the coupling reactions of aryl iodides and aryl alkynyl carboxylic acids to produce the diaryl alkynes in good yields without any additional ligand.

Nickel-catalyzed decarboxylative coupling reaction of alkynyl carboxylic acids and allyl acetates

The coupling reaction of aryl alkynyl carboxylic acids and allyl acetates was carried out in the presence of nickel catalyst to produce the allyl alkynes in good yields. The optimized condition is that alkynyl carboxylic acid (1.0equiv), allyl acetate (2.0equiv), Ni(OAc)2·4H2O (10mol%), AgOAc (10mol%), and zinc (1.0equiv) were reacted at 100°C for 0.5h. In addition, when allyl alcohol was employed instead of allyl acetate, the desired product was obtained in good yield. In addition, when the reaction was carried out in the presence of base such as DBU and Cs2CO3, the allene compounds were formed in good yield.

ChemInform Abstract: Synthesis of Aryl Alkynyl Carboxylic Acids and Aryl Alkynes from Propiolic Acid and Aryl Halides by Site‐Selective Coupling and Decarboxylation.

AbstractCoupling of aryl iodides with propiolic acid is carried out under conditions A) at 50°C to produce the corresponding aryl alkynyl carboxylic acids.

Synthesis of aryl alkynyl carboxylic acids and aryl alkynes from propiolic acid and aryl halides by site selective coupling and decarboxylation

The coupling of propiolic acid with aryl iodides afforded the aryl alkynyl carboxylic acids and aryl alkynes in generally good yields. Aryl alkynyl carboxylic acids were obtained when the reaction was performed in the presence of Pd(PPh3)2Cl2 (2.5mol%), dppb (5.0mol%) and DBU (5equiv) at 50°C. For the synthesis of the terminal aryl alkynes, the reaction was conducted in the presence of Pd(PPh3)2Cl2 (2.5mol%), dppb (5.0mol%), DBU (5.0equiv), and Cu(acac)2 (10mol%) at 25°C for 5h, and further reacted at 60°C for 6h.