Article
Chemistry, Organic
Lin Li, Xin-Lian Liu, Jin-Yan Liang, Yong-Yu He, Ai-Jun Ma, Wei-Feng Wang, Jin-Bao Peng
Summary: A palladium-catalyzed dicarbonylation reaction of alpha-iodo-substituted ACPs has been developed for the synthesis of carbamoyl-substituted indenones. Two carbonyl groups are incorporated into the product by cleaving the proximal C-C bond of the ACPs. A broad range of carbamoyl-substituted indenones are efficiently prepared with good to excellent yields.
Article
Chemistry, Applied
Jingyu Zhang, Wei Xia, Saskia Huda, Jas S. Ward, Kari Rissanen, Markus Albrecht
Summary: A copper(II)-catalyzed dearomative cyclization amination of N-(2-aminobenzoyl) indoles is described, yielding tetracyclic indolines under mild conditions with good yields. Tetracyclic 5a,6-dihydroindolo[2,1-b]quinazolin-12(5H)-ones are obtained in good to excellent yields (up to 99% yield) by N-Ts bond cleavage using trifluoromethanesulfonic acid (TfOH) mediation. The resulting compounds can be easily functionalized through simple synthetic methods.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Jun-Qi Zhang, Chunjiao Shen, Shihao Shuai, Ling Fang, Dandan Hu, Jiali Wang, Yu Zhou, Bukuo Ni, Hongjun Ren
Summary: A green and efficient approach for the difunctionalization of ynamides by merging the electrochemical and organoseleniumcatalyzed processes is described. This strategy features mild reaction conditions, broad functional group tolerance and high atom-economy, and requires no external chemical oxidant, providing a sustainable alternative for the synthesis of polysubstituted oxazoles.
Article
Chemistry, Multidisciplinary
Tianmei Zhang, Min Cai, Wenfeng Zhao, Mao Liu, Nan Jiang, Qingmei Ge, Hang Cong
Summary: We developed a practical and efficient electrochemical approach for the synthesis of pi-conjugated phosphonium salts through intramolecular annulation and C-P bond construction. This reaction took place under catalyst- and adscititious oxidant-free conditions at room temperature. A variety of substituted pi-conjugated phosphonium salt products were obtained with good functional group tolerance and yields. A gram-scale reaction demonstrated the potential of this protocol for practical applications. Preliminary mechanistic studies suggested the involvement of free radicals in this process.
Article
Chemistry, Organic
Shangyuan Wang, Jiajun Zhao, Jun Ying, Xiao-Feng Wu
Summary: This study developed a palladium-catalyzed one-pot two-step radical mediated carbonylative cyclization method to construct polycyclic 3,4-dihydroquinolin-2-(1H)-one scaffolds using perfluoroalkyl iodides and Mo-(CO)(6) with 1,7-enynes. Various polycyclic 3,4-dihydroquinolin-2-(1H)-one derivatives containing perfluoroalkyl and carbonyl units were synthesized with high yields. Moreover, modification of several bioactive molecules was demonstrated using this protocol.
Article
Chemistry, Physical
Lin-Jun Qi, Chong-Yang Shi, Peng-Fei Chen, Long Li, Gang Fang, Peng-Cheng Qian, Chao Deng, Jin-Mei Zhou, Long-Wu Ye
Summary: The study presents a novel gold-catalyzed 1,1-carboalkoxylation method for the synthesis of valuable cyclic compounds, enabling asymmetric synthesis through a chirality-transfer strategy. Further mechanistic insight into the distinct migration into gold carbenes is supported by theoretical calculations.
Article
Chemistry, Organic
Zhidong Jiang, Jianhui Zhou, Haoran Zhu, Hong Liu, Yu Zhou
Summary: A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported, generating diversely functionalized carbazole frameworks with good to excellent yields. The most notable feature is the formation of a novel [5 + 1] cyclization product, accompanied by the complete removal of acetyl and N,N-dimethyl groups from the substrates, rather than the expected [4 + 2] cyclization products.
Article
Multidisciplinary Sciences
Xiao-Biao Yan, Lun Li, Wen-Qiang Wu, Lun Xu, Ke Li, Yu-Cheng Liu, Hang Shi
Summary: The authors demonstrate a method to add alkanes with an amino functionality to olefins using a nickel catalyst that utilizes the amine itself as the hydride source, eliminating the need for an external hydride reagent. This approach allows for the production of valuable, complex structural motifs and chiral alpha-branched amines in organic synthesis. Additionally, the use of a P-chiral ligand further enhances the catalytic efficiency of the reaction.
NATURE COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Pallavi Singh, Kishor Kumar Chouhan, Arup Mukherjee
Summary: Ruthenium-catalyzed C-H activation is widely used in organic synthesis and molecular science, with a focus on the intramolecular functionalization which offers atom economy and easy purification of products. The development of new synthetic strategies in organic chemistry has gained significant interest in recent years.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Organic
Dusty Cadwallader, Dmytro Shevchuk, Tristan R. Tiburcio, Christine M. Le
Summary: This study presents a method for the synthesis of alkynamides through the cross-coupling of carbamoyl fluorides and alkynylsilanes catalyzed by tetrabutylammonium fluoride (TBAF). It achieves C-F bond cleavage under mild conditions without the need for strongly nucleophilic reagents and/or catalysts, offering advantages over transition-metal-catalyzed approaches in terms of tolerance to aryl halide moieties and complementary chemoselectivity.
Article
Chemistry, Organic
Bao-Le Qu, Bin Shi, Lin He, Jun-Wei Shi, Wen-Jing Xiao, Liang-Qiu Lu
Summary: Indoline skeletons are commonly found in natural compounds and drugs, making the synthesis of indolines a hot topic in synthetic chemistry. However, the asymmetric construction of indolines with chiral quaternary stereocenters poses a significant challenge. In this study, a solution to this problem is presented through copper-catalyzed asymmetric [4 + 1] cycloadditions of ethynylbenzoxazinones with sulfur ylides, generated in situ by photoinduced carbene transfer. The method allows for the synthesis of a wide range of chiral indolines with C2-quaternary stereocenters and good enantio- and diastereoselectivities (up to 19:1 dr and 96:4 er).
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Wei-Yang Ma, Coralie Gelis, Damien Bouchet, Pascal Retailleau, Xavier Moreau, Luc Neuville, Geraldine Masson
Summary: A highly enantio- and regioselective (3 + 2) formal cycloaddition catalyzed by a BINOL- and SPINOL-derived phosphoric acid is reported, leading to the synthesis of a wide variety of 2,3-disubstituted 2-aminoindolines with generally high yields and excellent enantioselectivities. The reaction showed moderate to complete diastereoselectivities in most cases, producing products with up to 98% yield and up to 99% ee.
Article
Chemistry, Organic
Wanjun Chen, Yaping Cheng, Tao Zhang, Yu Mu, Wenqi Jia, Guodu Liu
Summary: A nickel-catalyzed stereoselective asymmetric intramolecular reductive coupling of N-1,6-alkynones was reported, achieving efficient synthesis of versatile functionalized chiral pyrrolidines with high yields, excellent stereoselectivity, and enantioselectivity. The developed reaction is applicable to a broad substrate scope and can be scaled up to gram scale without loss of enantioselectivity. The study also investigated ligand effects and reaction mechanism, suggesting wider applications in organic synthesis and chemical biology, and potential for further explorations in new research fields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiyang Cao, Zhiguo Zhang, Jingya Li, Bingbing Shi, Mengjuan Li, Guisheng Zhang, Xingjie Zhang
Summary: An efficient and convenient method for the synthesis of indolo[2,1-a]isoquinolines was reported. This reaction involved the Rh(III)-catalyzed double aryl C(sp2)-H bond and N-H activation and annulation, with the presence of Cu(OAc)2 as the oxidant and under heating conditions. Notably, 1,3-diarylurea could serve as a precursor for the generation of two arylamine molecules, diverging from previous studies.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Rajshekhar A. Unhale, Milon M. Sadhu, Vinod K. Singh
Summary: A novel organocatalytic asymmetric formal [3 + 2] cycloaddition has been developed for the synthesis of biologically relevant chiral spiroisoindolinone-indolines with excellent yields and enantioselectivity under mild conditions.
Article
Chemistry, Multidisciplinary
Mallu Chenna Reddy, Masilamani Jeganmohan
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
Ravi Kiran Chinnagolla, Arjun Vijeta, Masilamani Jeganmohan
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Physical
Rajendran Manikandan, Padmaja Madasamy, Masilamani Jeganmohan
Article
Chemistry, Multidisciplinary
Ramasamy Manoharan, Ganesan Sivakumar, Masilamani Jeganmohan
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Multidisciplinary
Ganesan Sivakumar, Arjun Vijeta, Masilamani Jeganmohan
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Organic
Ramasamy Manoharan, Masilamani Jeganmohan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Rajendran Manikandan, Masilamani Jeganmohan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Nagnath Yadav More, Masilamani Jeganmohan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Nagnath Yadav More, Kishor Padala, Masilamani Jeganmohan
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Balu Ramesh, Masilamani Jeganmohan
Article
Chemistry, Organic
Rajendran Manikandan, Masilamani Tamizmani, Masilamani Jeganmohan
Article
Chemistry, Organic
Ramasamy Manoharan, Masilamani Jeganmohan
Article
Chemistry, Multidisciplinary
Mallu Chenna Reddy, Masilamani Jeganmohan
Article
Chemistry, Multidisciplinary
Nagnath Yadav More, Masilamani Jeganmohan
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Rajendran Manikandan, Masilamani Jeganmohan
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)