Article
Chemistry, Organic
Depeng Duan, Lu Song
Summary: The decarboxylative cross-coupling of oxamic acids with (hetero)aryl halides was achieved through the synergistic merger of organic photoredox with nickel catalysis. This new amide synthesis protocol is mild, operationally simple, and can transform a wide range of oxamic acids into the corresponding carbamides in good to excellent yields. It is also scalable and can be used for late-stage modification of complex molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Wen-Zhu Bi, Wen-Jie Zhang, Zi-Jie Li, Yuan-Hao He, Su-Xiang Feng, Yang Geng, Xiao-Lan Chen, Ling-Bo Qu
Summary: This study presents a general visible-light-promoted metal-free synthesis of secondary and tertiary thiocarbamates from thiosulfonates and N-substituted formamides. By using rhodamine B as a photocatalyst and tert-butyl hydroperoxide as an oxidant, a wide range of thiocarbamates can be obtained through direct thiolation of acyl C-H bonds under blue light irradiation at room temperature for 12 hours.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Sami Chniti, Laszlo Kollar, Attila Benyei, Agnes Dornyei, Attila Takacs
Summary: Novel N-substituted pyrrolo[3,4-b]quinoline-1,3-diones have been synthesized successfully through a highly selective palladium-catalyzed carbonylative imidazation-cyclization reaction. This method, applied for the first time to access original scaffolds, involves 3-bromo-2-iodoquinoline as a typical partner, primary amines, and atmospheric or high carbon monoxide pressure. The use of bidentate ligands such as XantPhos and dppp in atmospheric or high-pressure conditions provides a wide range of carbonylated compounds with good to excellent yields (up to 82%). Furthermore, new quinoline-2,3-dicarboxamides have been isolated as side products in very low yields and have been fully characterized. The solid state structures of three synthesized acridinimides have been unequivocally established by single-crystal XRD analysis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Peng Wang, Ji Yang, Kangkang Sun, Helfried Neumann, Matthias Beller
Summary: The direct palladium-catalyzed selective carbonylative coupling of less reactive aryl chlorides with primary and secondary amines is achieved using a palladium/Xantphos catalyst system and cesium chloride as an additive. This reaction shows high conversion for various aryl chlorides and good functional group compatibility.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Lingyun Yao, Jun Ying, Xiao-Feng Wu
Summary: A nickel-catalyzed carbonylative cyclization of 2-nitroalkynes and aryl iodides has been developed for the expedite construction of N-benzoyl indole scaffolds, with high efficiency and moderate to high yields. Control experiments were performed to better understand the reaction mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Ning Liu, Xianqing Wu, Jingping Qu, Yifeng Chen
Summary: A nickel-catalyzed aminocarbonylation reaction of aromatic iodides with (hetero)aryl anilines and alkyl amines under atmospheric CO pressure is reported. This reaction exhibits a broad substrate scope and excellent functional group tolerance, providing a convenient method for constructing amide analogues. Notably, amino alcohols can be selectively transformed into the corresponding amides under the current standard conditions without interfering with the hydroxyl group.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Sami Chniti, Laszlo Kollar, Attila Benyei, Attila Takacs
Summary: This research investigates the aminocarbonylation reaction of 6-iodoquinoline, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. The study shows that reaction conditions significantly influence the formation of amides and ketoamides, and by optimizing the conditions, selective synthesis of the desired products can be achieved.
Article
Chemistry, Organic
Jin-He Na, Xiang Liu, Jia-Wen Jing, Jing Wang, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A step-economical and efficient one-pot reaction was developed for the direct cross-coupling of aryl fluorosulfate with aryl bromide. This reaction, conducted at room temperature in THF solvent, does not require the use of preprepared/commercial organometallic reagents. By utilizing nickel catalyst, magnesium turnings, and lithium chloride, the desired biaryls were obtained in moderate to good yields with reasonable functional group compatibility.
Article
Chemistry, Multidisciplinary
Xueling Liu, Tongshun An, Zhiping Yin, Wenzhou Zhang
Summary: A new palladium-catalyzed reductive double carbonylation of nitroarenes with aryl halides has been developed for the synthesis of benzoxazin-4-ones. This method utilizes Mo(CO)(6) as a reductant and solid carbonyl sources, and can produce benzoxazin-4-one derivatives in moderate to good yields. Importantly, it avoids the use of toxic CO gas and is applicable for late-stage modification of estrone.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Siqi Wang, Shuwei Li, Liangcai Liu, Jun Ying, Xiao-Feng Wu
Summary: Amide-containing indolo-[2,1-a]isoquinoline scaffolds were synthesized by palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with nitro-arenes. Using Mo(CO)6 as the CO source and reductant, and nitroarenes as the nitrogen source, this reaction yielded various amide-containing indolo[2,1-a]isoquinoline derivatives in good yields. Additionally, the late-stage modifications of bioactive molecules using this protocol were demonstrated.
Article
Chemistry, Organic
Vinothkumar Ganesan, Seokyeong Moon, Sungho Yoon
Summary: A phenanthroline-based porous organic polymer supported heterogeneous Pd catalyst (Pd@Phen-POP) was synthesized by solvent knitting using dichloromethane as a linker source in the presence of Lewis acid AlCl3 catalyst for the Friedel-Crafts reaction. The catalyst effectively catalyzes the alkoxycarbonylation of various substituted aryl iodides with diverse alcohols, producing good to excellent yields. Due to its heterotic nature, the catalyst can be easily separated by simple filtration and recycled.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yuvraj A. Kolekar, Bhalchandra M. Bhanage
Summary: In this study, Pd/C-catalyzed oxidative aminocarbonylation and alkoxycarbonylation of unactivated aryl hydrazines were reported. This protocol provides a promising, simple, and effective approach for preparing esters and tertiary amides using environmentally benign solvent and recyclable catalyst.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ryota Isshiki, Miki B. Kurosawa, Kei Muto, Junichiro Yamaguchi
Summary: A Ni-catalyzed aryl sulfide synthesis method was developed using 2-pyridyl sulfide as the sulfide donor, eliminating the need for odorous and toxic thiols. The Ni/dcypt catalyst played a crucial role in the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, with mechanistic studies showing its ability to undergo oxidative additions and ligand exchanges simultaneously.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Francesco Messa, Andrea Nicola Paparella, Serena Perrone, Antonio Salomone
Summary: For the first time, Pd-catalyzed alkoxycarbonylation of aryl iodides has been investigated in phosphonium-based deep eutectic solvents under gas-free conditions using Mo(CO)(6) as the CO source. This method allows the efficient synthesis of ethylene glycol and glycerol esters with high yields (up to 99%), short reaction times, and mild reaction conditions, utilizing a remarkably low catalyst loading (0.5 mol%).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Fusheng Bie, Xuejing Liu, Han Cao, Yijun Shi, Tongliang Zhou, Michal Szostak, Chengwei Liu
Summary: The Pd-catalyzed double-decarbonylative synthesis of aryl thioethers involves an aryl exchange reaction between amides and thioesters, with amides serving as aryl donors and thioesters as sulfide donors. The use of Pd/Xantphos without any additives promotes aryl exchange by C(O)-N/C(O)-S cleavages, allowing for a wide variety of amides and sulfides to be used in the reaction.
Article
Chemistry, Organic
Manjunath S. Lokolkar, Pravin A. Mane, Sandip Dey, Bhalchandra M. Bhanage
Summary: An effective method for synthesizing 2-substituted indoles through addition/reductive cyclization in a one-pot tandem reaction has been presented. This method tolerates a wide range of functional groups and provides moderate to good yields. The gram-scale synthesis of 2-substituted indole has also been demonstrated. This protocol offers an alternative route for the synthesis of 2-substituted indoles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Manjunath S. Lokolkar, Manoj K. Pal, Sandip Dey, Bhalchandra M. Bhanage
Summary: In this study, a new palladium complex was synthesized and used as a catalyst for the synthesis of oxygen-containing heterocyclic flavones. The synthesized complex was characterized and found to remain active even at low loading.
Article
Chemistry, Organic
Tejas A. Gokhale, Sanjivani C. Gulhane, Bhalchandra M. Bhanage
Summary: This study explores the utilization of bio-derived feedstocks in the catalyst-free oxidative synthesis of N-formamides. The results reveal that 1,3-dihydroxyacetone and glyoxal have the best carbon efficiency and can be used to synthesize a library of N-formamides. The methodology has demonstrated high yields in both laboratory and pilot scale.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Vijay P. Mahajan, Yuvraj A. A. Kolekar, Bhalchandra M. M. Bhanage
Summary: This study presents a magnetically separable nickel catalyst supported on Fe3O4 for phenoxy carbonylation reactions to synthesize aryl esters. The use of o-chlorophenyl formate as a CO source and phenol as a coupling partner, along with the inexpensive nickel catalyst, are the main advantages of this method. The Ni/Fe3O4 catalyst showed excellent magnetic separability due to the superparamagnetic nature of Fe3O4 and could be reused for up to eight cycles with minimal drops in yield. The protocol demonstrated tolerance towards various functionalities of aryl iodides and provided moderate to good yields of the corresponding esters. The prepared Ni/Fe3O4 nanoparticles were characterized using analytical techniques such as FESEM, EDS, TEM, XRD, ICP-OES, and XPS.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Tejas A. Gokhale, Tejashri J. Sarda, B. Bhalchandra M. Bhanage
Summary: This study reports on the sunlight driven rapid photodegradation of Crystal Violet using Magnesium doped Zinc oxide nanostructures. Among them, 5% Mg-ZnO showed exceptional photocatalytic performance with the highest kinetic rate constant. Under optimized conditions, 30 mg of 5% Mg-ZnO exhibited >85% photodegradation efficiency of 10 ppm of Crystal Violet in a short period of time.
MATERIALS CHEMISTRY AND PHYSICS
(2023)
Article
Chemistry, Multidisciplinary
Yuvraj A. Kolekar, Vitthal B. Saptal, Bhalchandra M. Bhanage
Summary: This study successfully developed a catalyst with controllable activity and selectivity by combining mesoporous silica and N-rich melamine dendron through covalent grafting. The catalyst exhibited excellent catalytic activity for the oxidative carbonylative self-coupling reaction using N-formyl saccharin as a sustainable solid CO source and Cu as a co-catalyst.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Priyanka Jawale, Bhalchandra M. Bhanage
Summary: In this study, the synthesis of decanoate esters using immobilized lipase in deep eutectic solvent was investigated, and a suitable kinetic model was proposed. The best combination of DES and lipase for synthesizing propyl decanoate was found to be Gly:ChCl and Cal B, respectively. Response surface methodology was used to optimize reaction variables, and the activation energy was determined to be 14.59 kcal/mol. The study also showed that biocatalysts could be recycled for up to four cycles, and the reaction mechanism followed the Ping Pong Bi Bi mechanism. Molecular docking confirmed the acylation of the active site serine residue and strong hydrogen bonding between the substrate and active site.
JOURNAL OF THE INDIAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Satish M. Chauhan, Bhalchandra M. Bhanage
Summary: In this study, a catalyst-free synthesis method for quinazolinones using formic acid as a C1 source in the presence of triethylamine was developed. This simple and efficient approach provides a promising alternative to conventional routes and offers a sustainable solution for synthesizing quinazolinone derivatives.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Kasturi U. Nabar, Bhalchandra M. Bhanage, Sudam G. Dawande
Summary: An efficient, inexpensive, and environment-friendly method using copper sulfate as a catalyst and water as a green solvent has been developed for the N-arylation of amines with 1,3-cyclohexadione-derived aryliodonium ylides. Aromatic primary amines substituted with electron-donating or electron-withdrawing groups reacted smoothly, yielding diarylamines with good to excellent yields. Secondary amines also underwent N-arylation to give tertiary amines with moderate yields.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Vijay P. Mahajan, Yuvraj A. Kolekar, Bhalchandra M. Bhanage
Summary: This work presents a novel method for the synthesis of diaryl ketones through carbonylative homo-coupling reactions using a nickel catalyst supported on Al2O3. A heterogeneous Ni/Al2O3 catalyst was prepared and employed for the reaction of aryl iodides under carbon monoxide gas-free conditions. Good to excellent yields of symmetrical diaryl ketones were obtained using Co-2(CO)(8) as a carbon monoxide source. The catalyst demonstrated high stability with no significant loss of activity after five consecutive cycles.
Article
Chemistry, Physical
Tejas A. Gokhale, Prafull A. Jagtap, Bhalchandra M. Bhanage
Summary: This work presents a synthetic protocol for the synthesis of N-formamides using iron-based catalysis with magnetic Fe powder as the catalyst, achieving high yields and catalyst reusability.
Article
Chemistry, Multidisciplinary
Yuvraj A. A. Kolekar, Bhalchandra M. M. Bhanage
Summary: An efficient Pd/Cu-catalyzed self-carbonylation of arylhydrazines with CO and molecular oxygen has been developed, resulting in the synthesis of symmetrical biaryl ketones through C-N bond activation. The use of arylhydrazine hydrochlorides as green arylating agents allows for the release of nitrogen and water as byproducts. This protocol successfully suppresses the formation of aryl iodides and homo-coupled azobenzenes, even under favorable conditions, and allows for the synthesis of a library of symmetrical biaryl ketones with various functional groups in good yields under mild conditions.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Prafull A. Jagtap, Manjunath S. Lokolkar, Bhalchandra M. Bhanage
Summary: A simple, cost-effective, and straightforward method for the synthesis of 2,3-disubstituted indole scaffolds was developed. The reaction involves copper-mediated tandem hydroamination followed by C-H annulation of unprotected anilines with internal alkynes. The reaction proceeds well with Cu(OAc)(2)& BULL;H2O and trifluoroacetic acid (TFA), providing various substituted indole derivatives in moderate to good yields. The process is compatible with primary and secondary anilines as well as aromatic/aliphatic alkynes. High-purity copper nanoparticles can be recovered after the reaction, demonstrating the cost-effectiveness and environmentally benign nature of the protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Editorial Material
Chemistry, Multidisciplinary
Bhalchandra M. Bhanage
JOURNAL OF THE INDIAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Manjunath S. Lokolkar, Bhalchandra M. Bhanage
Summary: In this study, a palladium-catalyzed carbonylative synthesis method was developed for the one-pot synthesis of symmetrical xanthones. The protocol is simple, ligand- and additive-free, and provides moderate to good yields of the target compounds. It can also be extended for the synthesis of related derivatives.
