Article
Nanoscience & Nanotechnology
Cen Zhou, Rui Wang, Lang Gao, Xiaozhou Huang, Xiao Zhang
Summary: In this study, 3PTZ-POP, a photo-catalyst based on 3PTZ, was developed for visible-light-driven C-H functionalization reactions, resulting in the synthesis of 3,3-disubstituted 2-oxindoles bearing a pharmaceutically important CF3 moiety.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Multidisciplinary
Qing Yu, Yunyun Liu, Jie-Ping Wan
Summary: The perfluoroalkylsulfonylation in enaminone C-H bonds has been achieved by using molecular iodine promotion and stable, inexpensive sodium perfluoroalkyl sulfinates as coupling partners, leading to the stereoselective synthesis of E-configurated alpha-perfluoroalkylsulfonyl enaminones.
CHINESE CHEMICAL LETTERS
(2021)
Review
Chemistry, Multidisciplinary
Supriya Rej, Naoto Chatani
Summary: Considerable advances have been made in the field of C-H functionalization, with special interest in C-H borylation due to its wide applications. Transition-metal-catalyzed regioselective strategies have been developed, but the use of precious metals and contamination by metal precursors limit their application in large-scale synthesis. Recent trends involve the use of transition-metal-free systems.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Tao Zhang, Weijun Yao, Jie-Ping Wan, Yunyun Liu
Summary: A novel method for synthesizing 3-dithiocarbamyl chromones without transition metals has been developed, leading to a series of organic compounds with potential pharmaceutical activities by reacting specific substrates.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Multidisciplinary Sciences
Shao-Long Qi, Yu-Peng Liu, Yi Li, Yu-Xin Luan, Mengchun Ye
Summary: This study investigates a novel phosphine oxide-ligated Ni-Al bimetallic catalyst, which enables the regioselective activation of β-C-H bonds in hydroarylation reactions of alkynes.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Physical
Rahul Keshri, Debanjan Rana, Argha Saha, Shaeel Ahmed Al-Thabaiti, Abdulmohsen Ali Alshehri, Salem M. Bawaked, Debabrata Maiti
Summary: Transition-metal-catalyzed C(sp2)-H bond functionalization is a revolutionary strategy for efficient synthesis of complex heterocyclic frameworks. The use of free amine and alcohol as directing groups has shown significant advantages, allowing for the formation of C-C and C-heteroatom bonds and annulation cascades reactions. This review focuses on the utility of aromatic sp2-C-H functionalization directed by free amine and hydroxyl for constructing three to seven-membered N- and O-heterocycles.
Article
Chemistry, Organic
Yuan Shi, Kai Wang, Yuxin Ding, Yuanyuan Xie
Summary: A simple metal-free protocol for C-H trifluoromethylation of hydrazones via electrolysis was developed. This environmentally friendly transformation exhibited high efficiency, good tolerance, and the ability to scale-up functionalization, yielding the desired products in moderate to good yields. Additionally, different trifluoromethyl reagents were used to achieve high yields for substrates containing either electron-donating or electron-withdrawing groups. The radical mechanism was confirmed through control experiments.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Organic
Haritha Sindhe, Malladi Mounika Reddy, Karthikeyan Rajkumar, Akshay Kamble, Amardeep Singh, Anand Kumar, Satyasheel Sharma
Summary: Pyridine is a critical heterocyclic scaffold widely used in organic chemistry, medicines, natural products, and functional materials. New methodologies for the direct functionalization of pyridine scaffolds have been developed in the past two decades, including transition-metal-catalyzed C-H functionalization and rare earth metal-catalyzed reactions. This review discusses recent achievements in these areas and explores the underlying mechanisms.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tyler P. Pabst, Paul J. Chirik
Summary: Cobalt precatalysts for the meta-selective borylation of fluorinated arenes were developed, achieving high turnover and selectivity under optimized conditions. Deuterium kinetic isotope effects and stoichiometric experiments provided insights into the C-H activation step and the intermediate involved in catalysis. The results support kinetic control of C-H activation as the origin of meta-selectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Benedikt S. Schreib, Mina Son, Francoise A. Aouane, Mu-Hyun Baik, Erick M. Carreira
Summary: In this study, a Pd-catalyzed C-H alkenylation reaction of electronically unbiased allenes was reported, providing penta-1,2,4-triene products in up to 94% yield. The use of picolinamide directing group enabled the formation of allenyl-palladacycles, which subsequently participated in a turnover-limiting Heck-type reaction with electron-deficient alkene coupling partners. Additionally, picolinamide N,O-acetals were introduced as readily removable auxiliaries for C-H activation reactions, facilitating the efficient alkenylation of allenyl carbinol derivatives while maintaining the reactivity of the products.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Omar Sadek, Arnaud Le Gac, Nereida Hidalgo, Sonia Mallet-Ladeira, Karinne Miqueu, Ghenwa Bouhadir, Didier Bourissou
Summary: A new method has been developed for the synthesis of phosphine-boranes, featuring simplicity, efficiency, and broad substrate scope. The key intermediates were identified as P-stabilized borenium cations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kai Zhao, Jing-Yu Guo, Ting Guan, Ying-Xue Wang, Ji-Yu Tao, Yu Zhang, Qing-Hong Zhang, Kun Ni, Teck-Peng Loh
Summary: These methods utilize photocatalysis to efficiently incorporate fluorine-containing moieties into synthetically superior enamide scaffolds under mild and environmentally friendly conditions, with high regio- and stereoselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Lingli Liu, Yechun Wu, Xian Wu, Jin-Tao Yu, Changduo Pan
Summary: A photocatalytic method for the regio- and stereoselective beta-C(sp(2))-H sulfamoylation of enamides using commercially available sulfamoyl chlorides as sulfamoyl radical sources is developed. The reaction conditions are mild and metal-free with a broad substrate scope and excellent functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Jiefeng Hu, Xianyu Yang, Shasha Shi, Bo Cheng, Xiaoling Luo, Yu Lan, Teck-Peng Loh
Summary: This study presents a metal-free reaction system for C-H bond functionalization of aliphatic sulfonamides under mild conditions, offering a series of alpha,beta-unsaturated imines in good yields with high selectivities. Control experiments and detailed DFT calculations suggest a [2 + 2] cyclization/ring-cleavage reorganization process, opening up new possibilities for other related reorganization reactions.
Article
Chemistry, Multidisciplinary
Youhao Wei, Zheng Wang, Kaifeng Wang, Jiang-Kai Qiu, Zhaoshan Wang, Haotian Li, Xiu Duan, Kai Guo, Xiaoguang Bao, Xinxin Wu
Summary: This study reports a copper-catalyzed allenic C(sp(2))-H cyanation with exceptional site-selectivity, addressing the challenge in synthetic chemistry of functionalizing allenic C(sp(2))-H bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
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
Rajesh Akkineni, Sarma V. Markandeya, Avvari N. Prasad, Bhaskar Yamajala, B. Venkateswara Rao, Shankar Chaudhari, Deepak Kumar, Sandip T. Gadge, Bhalchandra M. Bhanage
Summary: An efficient and rapid method for synthesizing 1-3,3-dimethyl triazenes has been developed using in situ generated aryldiazonium tetrafluoroborate salts and DMF-DMA at room temperature. The reaction conditions are mild and yield high.
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.