Article
Chemistry, Multidisciplinary
Yan-Long Zheng, Pei-Pei Xie, Omid Daneshfar, Kendall N. Houk, Xin Hong, Stephen G. Newman
Summary: A new method has been developed to convert alkyl esters into alkyl ketones, resulting in the synthesis of 65 different alkyl ketones with various functional groups and heterocyclic structures. The study found that catalyst-controlled chemoselectivity could activate the C(acyl)-O bond in the substrate, while density functional theory calculations supported the mechanism of the nickel catalytic cycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Lara E. Zetzsche, Jessica A. Yazarians, Suman Chakrabarty, Meagan E. Hinze, Lauren A. M. Murray, April L. Lukowski, Leo A. Joyce, Alison R. H. Narayan
Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.
Article
Multidisciplinary Sciences
Bingnan Du, Chun-Ming Chan, Pui-Yiu Lee, Leong-Hung Cheung, Xin Xu, Zhenyang Lin, Wing-Yiu Yu
Summary: The authors developed diverse 2,2-difluorovinyl benzoates as versatile building blocks for modular synthesis of gem-difluoroenol ethers and gem-difluoroalkenes using nickel-catalyzed cross coupling. The method allows for late-stage functionalization of multifunctionalized bioactive molecules due to the diversity of the building blocks and excellent functional group tolerance.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Zahra Khorsandi, Abdol R. Hajipour, Mohamad Reza Sarfjoo, Rajender S. Varma
Summary: The nano-catalytic system described consists of magnetic nanoparticles as the core and edible natural ligands with functional groups as supports for cobalt species. It shows good catalytic activity in C-N cross-coupling reactions and demonstrates excellent efficiency and versatility in an array of coupling reactions. The system is easily accessible and has good recyclability for potential future applications.
Article
Biochemistry & Molecular Biology
Huimin Wang, Shuqin Zhang, Minling Xu, Gang Zou
Summary: Researchers have developed a practical and efficient Suzuki coupling reaction of phenols using trans-NiCl(o-Tol)(PCy3)(2)/2PCy(3) as a catalyst and tosyl fluoride as an activator. The compatibility of the nickel catalyst with tosyl fluoride and its fluorosulfate exchange reaction with C-Ar-OH are crucial for the direct use of phenols. Water improves the one-pot reaction significantly, and a variety of electronically and sterically diverse biaryls can be obtained in good yields using 3-10 mol% of the nickel catalyst.
Article
Chemistry, Applied
Sara Payamifar, Foad Kazemi, Babak Kaboudin
Summary: This study introduced a convenient nickel-catalyzed protocol for the Suzuki-Miyaura coupling reaction using a simple mixture of Ni(II) and unfunctionalized beta-cyclodextrin in water. The environmentally friendly and cost-efficient method allows the synthesis of biaryls from arylboronic acids and various aryl halides. The catalyst can be recycled for multiple runs with only a small decrease in catalytic activity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Shan Shan Ng, Wai Hang Pang, On Ying Yuen, Chau Ming So
Summary: This article provides an overview of the development of palladium-catalyzed coupling reactions and the effects of ligand properties on the chemoselectivity of aryl (pseudo)halides. The selectivity of coupling reactions can be significantly influenced by applying appropriate ligands. This review discusses the chemoselectivity of various catalysts and presents successful examples of sequential chemoselective coupling approaches, demonstrating the capacity of catalysts to regulate chemoselectivity and their implications for synthesizing valuable compounds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Paul O. Peterson, Matthew Joannou, Eric M. Simmons, Steven R. Wisniewski, Junho Kim, Paul J. Chirik
Summary: The synthesis and characterization of phenoxy(imine) iron(II) alkyl precatalysts for C(sp2)-C(sp3) Suzuki-Miyaura cross-coupling reaction is reported. This method utilizes mild alkoxide bases and nonpolar solvents to achieve high efficiency C(sp2)-C(sp3) bond formation with various aryl boronic esters and alkyl bromides. The study also highlights the compatibility of the precatalysts with base-sensitive functionality and the role of boronate intermediates in transmetalation.
Review
Chemistry, Inorganic & Nuclear
Zhilong Li, Chengyang Li, Yu Ding, Haohua Huo
Summary: The merger of nickel catalysis and photocatalysis has provided a transformative platform for the rapid assembly of molecular complexity. However, the development of enantioselective transformations in nickel photoredox catalysis remains challenging but holds great promise.
COORDINATION CHEMISTRY REVIEWS
(2022)
Article
Chemistry, Organic
Qianqian Lu, Haixing Guan, Yan-En Wang, Dan Xiong, Tingzhi Lin, Fei Xue, Jianyou Mao
Summary: A visible-light-promoted nickel/photoredox-catalyzed reductive cross-coupling reaction between vinyl bromides and benzyl chlorides has been reported, enabling the synthesis of a diverse array of enantioenriched allylic centers in good yields and high enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sheng-Qi Qiu, Yu Chen, Xiang-Jun Peng, Shi-Jiang He, Jun Kee Cheng, Yong-Bin Wang, Shao-Hua Xiang, Jun Song, Peiyuan Yu, Junmin Zhang, Bin Tan
Summary: In this study, we achieved the arene-alkene Suzuki-Miyaura coupling reaction between hindered aryl halides and vinyl boronates by designing appropriate ligands and reaction parameters. The axially chiral acyclic aryl-alkenes obtained exhibited remarkable efficiency, enantioselectivity, and E/Z selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Khadimul Islam, Vinay Arora, Vikas, Bedabara Nag, Akshai Kumar
Summary: Readily available and inexpensive bromide salt based on earth-abundant nickel has been used as a catalyst for the Suzuki coupling of various aryl halides with good yields and functional group tolerance under ambient conditions. The reaction follows a Ni(0)/Ni(II) catalytic cycle, where the oxidative addition of the aryl halide to Ni(0) is likely the rate-determining step.
Article
Chemistry, Organic
Xiaochun He, Jiangjun Liu, Gang Chen, Baojian Xiong, Xue Xiao, Lei Chen, Xuemei Zhang, Lin Dong, Xuelei Ma, Zhong Lian
Summary: A nickel-catalyzed cross-electrophile coupling of allylic acetates and gem-difluorovinyl tosylate has been developed. This reaction enables the synthesis of allylic gem-difluoroolefins via C(sp(3))-C(sp(2)) cross-electrophile coupling and proceeds under mild reaction conditions, providing a variety of allylic gem-difluorovinyl arenes in moderate to good yields. Mechanistic studies reveal the involvement of two different Ni(0)/Ni(II) catalytic cycles.
Article
Chemistry, Organic
Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: The direct cross-coupling of diaryl sulfoxides with aryl bromides via C-S bond cleavage was achieved using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF. This reaction showed a wide range of substrates and could be used for gram-scale synthesis. The one-pot reaction is operationally simple and economically efficient.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Chung-Hao Yang, Yi-Hung Liu, Shie-Ming Peng, Shiuh-Tzung Liu
Summary: A hetero-binuclear complex Ir-Pd was obtained by the reaction between iridium complex and (CH3CN)PdCl2 via ortho-metallation. This complex showed excellent catalytic activity for Suzuki-Miyaura and Sonogashira cross coupling reactions under blue LED irradiation. The effects of photochemical conditions on these coupling reactions catalyzed by Ir-Pd were studied.
MOLECULAR CATALYSIS
(2022)
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)