Article
Polymer Science
Chang-An Wang, Wei Zhao, Yan-Wei Li, Yin-Feng Han, Jian-Ping Zhang, Qun Li, Kun Nie, Jian-Guo Chang, Feng-Shou Liu
Summary: A bulky N-heterocyclic carbene functionalized conjugated microporous polymer catalyst has been developed through post-synthesis method, showing high catalytic efficiency and broad application potential.
Article
Chemistry, Physical
Zahid Nawaz, Nevin Gurbuz, Muhammad Naveed Zafar, Namik Ozdemir, Uzma Habib, Kalsoom Jan, Ismail Ozdemir
Summary: The research aims to synthesize homogeneous catalysts by starting from novel precursors to form N-heterocyclic carbene (NHC) ligands, and subsequently synthesizing Pd(NHC)-PEPPSI type complexes. The structure of all synthesized ligands and complexes was confirmed using various spectroscopic techniques, with some compounds confirmed by X-ray. These complexes were found to be significantly active as catalysts in the C-C cross-coupling reaction.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Biochemistry & Molecular Biology
Md. Mahbubur Rahman, Qun Zhao, Guangrong Meng, Roger Lalancette, Roman Szostak, Michal Szostak
Summary: In this Special Issue, a new highly hindered Pd(II)-NHC precatalyst, [IPr#-PEPPSI], was synthesized and characterized for cross-coupling reactions. Commercialized in collaboration with MilliporeSigma, this catalyst provides broad access to reaction screening and optimization for academic and industrial researchers. The broad activity of [IPr#-PEPPSI] in various bond activations and its steric and electronic properties were evaluated, indicating its potential for application in chemistry research.
Article
Chemistry, Organic
You-Wei Wu, Mu-Xiang Chen, Yan Li, Lu-Min Hu, Lili Zhao, Zhenhua Jia, Xuefei Zhao, Xu-Hong Hu
Summary: A distinct protocol for secondary amide formation through a catalyst- and additive-free cross-coupling of isocyanates with triarylboranes has been described, avoiding the use of moisture-sensitive organometallics, transition metals, or any additives, and accessing valuable amides through aryl migration.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Biochemistry & Molecular Biology
Rida Noor, Ameer Fawad Zahoor, Muhammad Irfan, Syed Makhdoom Hussain, Sajjad Ahmad, Ali Irfan, Katarzyna Kotwica-Mojzych, Mariusz Mojzych
Summary: Hiyama cross-coupling is a versatile reaction that enables the construction of carbon-carbon bonds in synthetic organic chemistry. By coupling organosilicons with organic halides using transition metal catalysts, good yields and high enantioselectivities can be achieved. In recent years, researchers have made significant progress in using the Hiyama coupling reaction for the synthesis of diversified natural products and pharmaceutical drugs.
Article
Chemistry, Physical
Guang-Yan Xing, Ya-Cheng Zhu, Deng-Yuan Li, Pei-Nian Liu
Summary: On-surface synthesis, a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials, has greatly enriched fundamental science and technology. Achieving high selectivity of covalent coupling reactions remains challenging due to the complicated reactivity of organic groups and irreversibility of covalent bonds. Only a few on-surface covalent coupling reactions are frequently used, and this Perspective focuses on the development and synthetic applications of on-surface cross-coupling reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Applied
Meliha cetin Korukcu, Samet Can
Summary: A series of air-stable NHC-Pd-PEPPSI-type complexes with unsymmetrical NHC ligand and a phenyl group in its backbone were successfully synthesized with high yields (82%-94%). The complexes were characterized by various spectroscopic techniques, including H-1 NMR, C-13 NMR, FT-IR spectroscopy, and HRMS. The crystal structure of the complexes was determined using single-crystal X-ray diffraction, showing a slightly distorted square planar geometry around the metal centre. The complexes exhibited excellent catalytic activities in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions under low catalyst loadings.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xinlan A. F. Cook, Loic R. E. Pantaine, David C. Blakemore, Ian B. Moses, Neal W. Sach, Andre Shavnya, Michael C. Willis
Summary: Heteroaromatic sulfinates are effective nucleophilic reagents in Pd-0-catalyzed cross-coupling reactions with aryl halides. Base-activated, latent sulfinate reagents, such as beta-nitrile and beta-ester sulfones, have been introduced to address challenges in purifying and solubilizing metal sulfinate salts, as well as their tolerance to multi-step transformations. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration and amenable to scale-up processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jun Chen, Yu-Jie Liang, Peng-Zi Wang, Guo-Qing Li, Bin Zhang, Hao Qian, Xiao-Die Huan, Wei Guan, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Myuto Kashihara, Yoshiaki Nakao
Summary: Cross-coupling reactions using nitroarenes as electrophiles have gained attention due to their ease of accessibility and potential advantages over haloarenes. Recent research has focused on developing new catalyst systems and reaction conditions to improve the efficiency and practicality of these reactions, with promising results in diversifying bond-forming reactions and reducing catalyst loading. Research in this field is expected to continue growing as the utility of nitroarenes in organic synthesis is reevaluated.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Review
Chemistry, Multidisciplinary
Xinlan A. F. Cook, Antoine de Gombert, Janette McKnight, Loic R. E. Pantaine, Michael C. Willis
Summary: This review focuses on the methods developed for the challenging coupling of 2-pyridine nucleophiles with (hetero)aryl electrophiles, ranging from traditional cross-coupling processes to alternative nucleophilic reagents and novel main group approaches.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Liang Gong, Qian Zhang, Demeng Xie, Wei Zhang, Shi-Yang Xu, Xia Zhang, Dawen Niu
Summary: A Ni-catalyzed Negishi coupling reaction can prepare 1,2-dialkyl enol ethers in a stereoconvergent fashion, using alpha-oxy-vinylsulfones as electrophiles. This reaction shows unique selectivity and general applicability, indicating potential for further use in cross-coupling reactions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Lukas Hoff, Simon D. Schnell, Andrea Tomio, Anthony Linden, Karl Gademann
Summary: A silver-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids was presented in this study. It was found that electronic modification of the dppf ligand played a crucial role in achieving good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were successfully prepared, with yields up to 87%.
Review
Chemistry, Multidisciplinary
Emily K. Reeves, Emily D. Entz, Sharon R. Neufeldt
Summary: Chemodivergent cross-couplings refer to reactions in which one potentially reactive functional group can be made to react based on choice of conditions. Factors influencing selectivity include catalyst ligation state, solvent polarity, and metal identity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Inorganic & Nuclear
Zahid Nawaz, Nevin Gurbuz, Muhammad Naveed Zafar, Muhammad Nawaz Tahir, Muhammad Ashfaq, Huseyin Karci, Ismail Ozdemir
Summary: The study successfully synthesized five new Pd PEPPSI-type complexes with NHC spectator ligands, which showed significant activity in direct arylation reactions. Structural details were further confirmed through single crystal X-ray diffraction study, showing good results with just 1 mol % catalyst loading in two hours.
Review
Chemistry, Inorganic & Nuclear
Colin Diner, Michael G. Organ
Article
Chemistry, Multidisciplinary
Narayan Sinha, Pier Alexandre Champagne, Michael J. Rodriguez, Yu Lu, Michael E. Kopach, David Mitchell, Michael G. Organ
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Christopher Lombardi, Richard P. Rucker, Robert D. J. Froese, Sepideh Sharif, Pier Alexandre Champagne, Michael G. Organ
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Biochemistry & Molecular Biology
Omar M. El-Halfawy, Tomasz L. Czarny, Ronald S. Flannagan, Jonathan Day, Jose Carlos Bozelli, Robert C. Kuiack, Ahmed Salim, Philip Eckert, Richard M. Epand, Martin J. McGavin, Michael G. Organ, David E. Heinrichs, Eric D. Brown
NATURE CHEMICAL BIOLOGY
(2020)
Review
Chemistry, Multidisciplinary
Philip Eckert, Sepideh Sharif, Michael G. Organ
Summary: Negishi first reported the cross-coupling of organozinc nucleophiles with aryl halides in 1977. The importance of salt additives in this process was overlooked for decades until 2006, leading to debate in the catalysis community.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jee Seong Kwak, Nour Bizarri, Sepideh Sharif, Wenyao Peter Zhang, Debasis Mallik, Michael G. Organ
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Fred U. Nnamdi, Colin Diner, Pier Alexandre Champagne, Michael G. Organ
Summary: Two similar tridentate directing groups derived from glycine and 8-aminoquinoline showed significantly different efficiencies in the palladium-catalyzed anti-Markovnikov hydrofunctionalization of 4-pentenylamine. Computational investigation revealed that the protonation state and charge of the substrate-metal complex prior to nucleopalladation are crucial for the reactivity difference between these isomeric auxiliaries. These findings led to the design of a directing group that can undergo Pd-catalyzed hydrofunctionalization under relatively mild conditions, down to room temperature.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Analytical
Jee Seong Kwak, Wenyao Peter Zhang, Debasis Mallik, Michael G. Organ
Summary: Chiral active pharmaceutical ingredients have better binding specificity to chiral biological targets than achiral ones, but synthesizing them requires optimizing multiple quality attributes simultaneously. The multidimensional liquid chromatographic tool allows for the measurement of multiple attributes from a single injection, aiding scientists in identifying unknown impurities accurately.
ANALYTICAL CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Mathieu A. Morin, Wenyao (Peter) Zhang, Debasis Mallik, Michael G. Organ
Summary: Process analytical technology (PAT) is a system that helps chemists understand and control manufacturing processes by combining analytical devices and mathematical models to ensure product quality. Continuous manufacturing in industries like pharmaceuticals requires the development of PAT tools suitable for flow reactors, with innovative sampling and analysis methods being essential.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Volodymyr Semeniuchenko, Wilfried M. Braje, Michael G. Organ
Summary: NaBHT, paired with Pd-NHC catalysts, is effective in solvent-free cross-coupling amination. Its mild nucleophilicity and antioxidant properties make it more effective in handling functional group incompatibilities.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Medicinal
Sean D. Workman, Jonathan Day, Maya A. Farha, Sara S. El Zahed, Chris Bon, Eric D. Brown, Michael G. Organ, Natalie C. J. Strynadka
Summary: The research team provided a structural model for the inhibition of UppS, a potential target for antibiotic development, and demonstrated the enhanced effect of a compound and its derivative on antibiotics with structural rationales. They also presented an improved structural model of clomiphene's inhibition of UppS, laying a foundation for future structure-guided drug design of more potent UppS inhibitors.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Volodymyr Semeniuchenko, Sepideh Sharif, Jonathan Day, Nalin Chandrasoma, William J. Pietro, Jeffrey Manthorpe, Wilfried M. Braje, Michael G. Organ
Summary: (DiMeIHept(Cl))Pd, a hyper-branched N-aryl Pd NHC catalyst, is efficient at performing amine arylation reactions in solvent-free conditions, allowing for the synthesis of various aniline derivatives, including those containing alcohol moieties, on a multi-gram scale.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Volodymyr Semeniuchenko, Jeffrey S. Ovens, Wilfried M. Braje, Michael G. Organ
Summary: NaBHT is a valuable medium-strength base for various applications, especially in Buchwald-Hartwig coupling reactions. The structures of solvent-free NaBHT and its various solvates were determined using single-crystal X-ray diffraction. It was found that NaBHT has a unique inorganic polymer structure in its solvent-free form, different from other sodium phenolates, which may contribute to its reductive properties.
Article
Chemistry, Multidisciplinary
Aliakbar Mohammadzadeh, Sepideh Sharif, Volodymyr Semeniuchenko, Norman Townsend, Andrew D. Corbett, Michael G. Organ
Summary: A reactor has been designed specifically for lithium aluminum hydride reductions in flow, allowing strict control over the entire process to ensure safety and efficiency.
JOURNAL OF FLOW CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Philip Eckert, Michael G. Organ
Summary: Bulky Pd-N-heterocyclic carbene (NHC) catalysts have higher reactivity in cross-coupling reactions, and chlorinating the NHC core further increases the reactivity. However, a reversal of these trends is observed in the cross-coupling of primary alkyl electrophiles and nucleophiles.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
