Article
Chemistry, Multidisciplinary
Jin Jiaping, Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: Here, we report an enantioselective protocol for the chiral phosphoric acid-catalyzed addition of 3-arylisoxazol-5-amines to highly reactive 3-methide-3H-pyrroles. This protocol provides a diverse range of heterotriarylmethanes bearing an amino acid moiety in good yields (up to 97%) and high enantioselectivities (up to 93% ee) under mild conditions. The utilization of a chiral spirocyclic phosphoric acid is crucial in converting the initial 1H-pyrrol-3-yl carbinols into reactive 3-methide-3H-pyrroles and achieving the desired enantioselective transformation.
Article
Chemistry, Multidisciplinary
Ning Li, Wenjing Lu, Weizhi Gu, Kuiliang Li, Jindong Li, Yangmian Lu, Zhenggen Zha, Zhiyong Wang
Summary: An asymmetric Michael/hemiketalization reaction was developed between isatin-derived beta, gamma-unsaturated alpha-ketoesters and 4-hydroxycoumarins in aqueous media. A series of chiral spirooxindole derivatives with an all-carbon quaternary stereogenic center were obtained in high yields (up to 93%) and excellent enantioselectivities (up to 98%).
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ran Chen, Qian-Qian Yan, Shao-Jun Hu, Xiao-Qing Guo, Li-Xuan Cai, Dan-Ni Yan, Li-Peng Zhou, Qing-Fu Sun
Summary: By varying the metal/ligand ratio, dinuclear triple helicates or mononuclear pincer complexes can be selectively obtained from the same chiral bis-tridentate ligand, with both complexes demonstrating catalytic properties in asymmetric Friedel-Crafts alkylation reactions due to the presence of open metal sites.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Esra Dundar, Cihangir Tanyeli
Summary: A series of chiral bifunctional squaramide organocatalysts were evaluated for their application in Friedel-Crafts alkylation of indoles, showing high enantioselectivity and moderate yields. This new asymmetric transformation provides a simple, efficient, clean, and environmentally friendly route for chemical synthesis.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Shuang-Liang Liu, Liming Zhou, Shaoming Fang, Ru Zhao, Menglong Li, Haoran Yang
Summary: The Rh(III)-catalyzed addition of indole C2-H bond to nitroalkenes at room temperature and atmospheric pressure is reported, providing a convenient method for the synthesis of a wide range of 2-(2-nitroalkyl)indoles in high yield and selectivity. Pyrrole derivatives were also successfully employed in the Friedel-Crafts alkylation reaction. The obtained nitroalkane products could be further transformed into structurally diverse and valuable indole derivatives. Control experiments were conducted and a plausible mechanism was proposed.
Article
Chemistry, Organic
Zeynep Dilsad Susam, Bilge Deniz Ozcan, Enis Kurtkaya, Erol Yildirim, Cihangir Tanyeli
Summary: In this study, bifunctional quinine-derived organocatalysts were used to catalyze the asymmetric Friedel-Crafts/S(N)2 domino reaction, resulting in enantiomerically enriched products. Density functional theory calculations were also performed to explain the stereoselectivity of the products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Kosuke Nakashima, Sumire Hanamura, Aoi Imamura, Yasuyuki Matsushima, Shin-ichi Hirashima, Tsuyoshi Miura
Summary: This study investigates the asymmetric Friedel-Crafts alkylation of indoles with alpha,beta-unsaturated trifluoromethyl ketones using a squaramide organocatalyst. The squaramide organocatalyst efficiently promotes the reaction, yielding products with both indole motif and trifluoromethyl group in high yields and excellent enantioselectivities (up to 99% ee). The transformation of the obtained adduct to a chiral spiro indoline 3-one is also demonstrated.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Takanori Shibata, Mio Sasaki, Masafumi Kojima, Mamoru Ito
Summary: The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with alpha,beta-unsaturated carbonyl compounds proceeded with high enantioselectivity, yielding chirally functionalized pyrroles and indoles as formal C-H conjugate adducts. The reaction mechanism was further investigated through deuterium labeling experiments.
Article
Chemistry, Organic
Zhenwei Wu, Suvratha Krishnamurthy, K. S. Satyanarayana Tummalapalli, Jon C. Antilla
Summary: This study developed a chiral calcium phosphate-catalyzed enantioselective amination of 2-oxindoles with dibenzyl azodicarboxylate, resulting in consistently high yields and excellent enantioselectivity. This method features low catalyst loading and high catalytic efficiency, and its practical value is demonstrated through scale-up experiments and catalyst recovery and reuse trials.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qian-Yi Wang, Teng-Fei Liu, Li-Feng Chu, Yun Yao, Chong-Dao Lu
Summary: In the presence of a chiral spiro phosphoric acid catalyst, the asymmetric reaction of disubstituted ketenes with N-H pyrroles occurred to afford enantioenriched C-acylated pyrroles bearing alpha-stereogenic carbon centres. This reaction represents a rare example of catalytic asymmetric reaction of ketenes with carbon-based nucleophiles, with significant research implications.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Velu Saravanan, Arasambattu K. Mohanakrishnan
Summary: A one-pot synthesis of aryl- and heteroaryl-annulated carbazoles was achieved from 2/3-bromomethylindoles, along with a bis-domino reaction of 2,5-bis(bromomethyl)pyrrole with selected heteroarenes. The synthesized thienocarbazoles and thienodibenzofurans were successfully utilized for a second-generation domino reaction.
SYNTHESIS-STUTTGART
(2021)
Article
Biochemistry & Molecular Biology
Mohammad Shahidul Islam, Abdullah Saleh Alammari, Assem Barakat, Saeed Alshahrani, Matti Haukka, Abdullah Mohammed Al-Majid
Summary: Five new C-2-symmetric chiral ligands were synthesized from enantiopure amino alcohols, and used for Friedel-Crafts asymmetric alkylation. The bis(oxazolinyl)thiophene ligands showed higher efficiency in inducing asymmetric alkylation compared to bis(imidazolinyl)thiophene analogues.
Article
Chemistry, Organic
Cheng Huang, Zhifei Zhao, Shiwu Li, Jixing Zhao, Leifang Wu, Chengzhi Gu
Summary: A highly enantioselective conjugate addition has been developed for the reaction between indolizine and its analogues with alpha,beta-unsaturated 2-acyl imidazoles. This method provides excellent yields and enantioselectivities, overcoming the limitations of organocatalysts in controlling stereoselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Ryoya Tajima, Takaaki Saito, Takayoshi Arai
Summary: The conventional acid-catalyzed aza-Friedel-Crafts reaction of phenols with imines typically shows ortho-selectivity. However, a chiral bis(imidazolidine) pyridine (PyBidine)-Ni(OAc)(2) catalyst can switch the regioselectivity to para-selectivity. This switch is facilitated by the bulky PyBidine-Ni(OAc)(2) catalyst with a Ph2CHCH2 substituent, resulting in highly para-selective aza-Friedel-Crafts reactions (up to 99:1 para/ortho selectivity).
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.
Article
Chemistry, Physical
Zi-Ye Liu, Qian-Yu Wang, Ji-Ming Hu
Summary: In this study, a layered carbon dot composite catalyst (NiFe LDH@CDs) was prepared using a one-step coprecipitation method, without the need for heating or hydrothermal treatment. The CD-functionalized catalyst facilitated rapid charge transfer and accelerated the oxygen evolution reaction. Additionally, the heterojunction structure formed between NiFe LDH and CDs efficiently suppressed photoelectron-hole recombination.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Rohit Kumar, Ankit Kumar Srivastava, Palaniyappan Nagarasu, Vedichi Madhu, Ekambaram Balaraman
Summary: We designed and synthesized a NN-CoII bidentate complex and used it for the amination of alcohols under mild and solventless conditions. The complex exhibited good reactivity towards both primary and sterically hindered secondary alcohols, providing high yields of amines. The pyrazole moiety in the ligand played a crucial role in the reaction. Furthermore, we demonstrated the reusability of the complex as a homogeneous cobalt catalyst.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Shivanand Chettri, Liang-Ting Wu, Sagarmani Rasaily, Debesh Sharma, Bikram Gurung, Rajani Dewan, Sudarsan Tamang, Jyh-Chiang Jiang, Anand Pariyar
Summary: Replicating the enzymatic surface microenvironment in vitro is challenging, but constructing an analogous model could facilitate our understanding of surface effects and aid in developing an efficient bioinspired catalytic system. In this study, five unique Cu2O morphologies were generated, and the surface morphology variations were found to be a consequence of differences in the exposure of low-index facets. The reactivity of Cu2O was found to be influenced by the proportion of {110} planes, with r-Cu2O exhibiting the highest reactivity.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Yong Tang, Jianhao Qiu, Dingliang Dai, Guanglu Xia, Lu Zhang, Jianfeng Yao
Summary: Defect engineering has been shown to improve the photocatalytic performance. This study investigated the use of defect-rich UiO-66-NH2 wrapped by ZnIn2S4 as a catalyst for photocatalytic H2O2 production. The defects in UiO-66-NH2 enhanced O-2 adsorption and charge separation, leading to higher H2O2 yield. The insights from this work can advance the research in defect engineering of MOFs and photocatalytic H2O2 synthesis.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Ruiyang Qu, Shuxin Mao, Jana Weiss, Vita A. Kondratenko, Evgenii V. Kondratenko, Stephan Bartling, Haifeng Qi, Annette-Enrica Surkus, Kathrin Junge, Matthias Beller
Summary: The hydrogenation of amides, a challenging reaction usually performed at high temperatures, has been achieved under milder conditions using a new Pt-MoOx/TiO2 catalyst. This catalyst system enables the selective hydrogenation of various amides and imides.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Xiaoran Niu, Ao Wang, Lei Tong, Lei Wang, Yuan Kong, Chenliang Su, Hai-Wei Liang
Summary: This study introduces a novel intermetallic PdCu3 catalyst supported on defective nanodiamond-graphene (ND@G), which exhibits high selectivity (95%) and remarkable activity (turnover frequency: 2940 h(-1)), six times higher than that of the commercial Lindlar catalyst.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Review
Chemistry, Physical
Zhiyuan Zheng, Yiming Yue, Hongying Zhuo, Qinggang Liu, Yanqiang Huang
Summary: This review presents the recent research advances on single-atom catalysis for deep reduction of CO2. Detailed introductions and summaries were classified into three categories based on proton-coupled multi-electron transfer approaches: strengthening metal-support interaction, rational design and regulation of coordination environment, and development of SACs with multi-atom active sites. The challenges and future research directions in the field of SACs for CO2 reduction are also proposed.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
Shiv Kumar, Paramita Datta, Anup Bhunia, Swadhin K. Mandal
Summary: This article reports a transition-metal-free process for in situ denitrogenation of tosylhydrazones, resulting in the production of various sulfones. The authors used a phenalenyl-based odd alternant hydrocarbon as a photoredox catalyst, which acted as a potent oxidant to facilitate the denitrogenation reaction. The method showed wide functional-group tolerance and high yields, making it suitable for late-stage modification of natural products.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
Article
Chemistry, Physical
L. A. Luque-Alvarez, J. Gonzalez-Arias, F. Romero-Sarria, T. R. Reina, L. F. Bobadilla, J. A. Odriozola
Summary: Currently, the production of acetic acid through the carbonylation reaction of methanol has limitations, leading to the exploration of alternative methods using heterogeneous catalysts. This study investigates the methanol carbonylation reaction over a Cu-H-MOR catalyst and proposes a reaction mechanism based on the catalytic behavior and performance of the catalyst. The results provide insights into the reaction mechanism and the involvement of acid and redox centers.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)
