Article
Chemistry, Multidisciplinary
Jie Gao, Rui Ma, Lu Feng, Yuefeng Liu, Ralf Jackstell, Rajenahally V. Jagadeesh, Matthias Beller
Summary: This study introduces a general protocol for the selective hydrogenation and deuteration of alkenes, utilizing a specific nickel-graphitic shell-based core-shell-structured catalyst to achieve high yields of corresponding alkanes and deuterium-labeled alkanes at ambient conditions. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated through gram-scale reactions and efficient catalyst recycling experiments.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Wen-Jie Kang, Bo Li, Meng Duan, Guangxing Pan, Weiqiang Sun, Aishun Ding, Yanbin Zhang, K. N. Houk, Hao Guo
Summary: The study found that using TfOH as a co-catalyst can tune the properties of TX to make it a photoredox catalyst with highly enhanced oxidative capability, successfully applied in the hydrogenation of alkenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Josep Mas-Rosello, Christopher J. Cope, Eric Tan, Benjamin Pinson, Alan Robinson, Tomas Smejkal, Nicolai Cramer
Summary: Cyclometalated cyclopentadienyl iridium(III) complexes are efficient catalysts in the hydrogenation of oximes, with alkoxy-substituted aryl ketimine ligands providing the best catalytic performance. The stable iridium C,N-chelation is crucial for the catalytic activity, and the hydrogenation system demonstrates high functional group compatibility.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Bram B. C. Peters, Pher G. Andersson
Summary: The translation discusses the application of chiral iridium complexes derived from Crabtree's catalyst in modern hydrogenation of olefins. Despite the pH neutrality of these precatalysts, the reaction mixtures become acidic under hydrogenation conditions. The paper explores the implications of this acidity on asymmetric hydrogenation and suggests opportunities for utilizing or eliminating the generated Bronsted acid.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Inorganic & Nuclear
Raill R. Quinonez-Lopez, Sara A. Cortes-Llamas, J. Roberto Estrada-Flores, Jose G. Alvarado- Rodriguez, Oscar Blanco-Alonso, A. Aaron Peregrina-Lucano, Elvia Becerra-Martinez, I. Idalia Rangel-Salas
Summary: Heteroleptic [RhIIICp*(NHC)] and [IrIIICp*(NHC)] complexes with a N-amino acid functionality derived from imidazolium salts were synthesized and characterized. The structure of [RhCp*{kappa 2(C,O)-NHC}Cl] complex 3f was discussed as a pair of diastereomers. The catalysts showed good yields for the transfer hydrogenation of ketones in basic propan-2-ol, and a chromatographic method for measuring compounds in the reaction was validated. These Rh and Ir complexes provide a new approach in developing catalysts based on classical NHC precursors.
Article
Chemistry, Multidisciplinary
Yu Nie, Qianjia Yuan, Wanbin Zhang
Summary: The design and synthesis of chiral ligands play a vital role in asymmetric catalytic reactions. Our group has developed a novel chiral PHOX ligand with an axis-unfixed biphenyl backbone, which exhibits interesting coordination behavior and excellent chiral inducing ability in various transition-metal-catalyzed asymmetric reactions. This personal account provides an overview of the design and applications of our developed BiphPHOX ligand, aiming to inspire the exploration of novel ligands and related reactions.
Article
Chemistry, Multidisciplinary
Rafal Kusy, Karol Grela
Summary: In this review, recent advances in the application of metal nanoparticles in the selective hydrogenation of C-C double bonds are presented. The reduction methods of alkenes, arenes, and aromatic heterocycles are focused on and classified according to the transition metals used as catalysts. Most of the described systems involve direct hydrogenation, which is important for industrial processes. Additionally, convenient transfer hydrogenation protocols have been developed for laboratory purposes. Some methods exhibit excellent chemoselectivity, making them ideal for synthesizing compounds with reducible functional groups. The use of earth-abundant metals as catalysts has also been explored.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Wei Zhao, Wenji Wang, Huan Zhou, Qishan Liu, Zhiqing Ma, Haizhou Huang, Mingxin Chang
Summary: A one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Bronsted acid activation strategy is reported. The reaction exhibits high stereoselectivity and can be used to synthesize indolizidines and quinolizidines. Experimental and theoretical studies reveal that chloride anion and noncovalent interactions play important roles in determining the stereoselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Haibo Wu, Hao Su, Erik J. Schulze, Bram B. C. Peters, Mark D. Nolan, Jianping Yang, Thishana Singh, Marten S. G. Ahlquist, Pher G. Andersson
Summary: The study presents a highly efficient desymmetrization of 1,4-dienes through iridium-catalyzed site- and enantioselective hydrogenation, allowing the installation of two adjacent stereogenic centers. High yields and excellent selectivities were achieved for a range of substrates, and the methodology was demonstrated by synthesizing key intermediates of natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jing Wang, Wenji Wang, Xiongyu Yang, Jingwen Liu, Haizhou Huang, Mingxin Chang
Summary: In this study, a practical homogeneous direct reductive amination (DRA) procedure using iridium catalysis was reported. The reaction conditions were mild and additive-free, allowing for the formation of structurally and functionally diverse amine products, including drugs and compounds from late-stage manipulation. DFT studies revealed that the reaction proceeds via an outer-sphere H-addition pathway with important roles played by pi-pi interactions and H-bonding.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Ke Zhang, Charles B. Musgrave, Diane A. Dickie, William A. Goddard, T. Brent Gunnoe
Summary: The influence of different capping arene ligands on the catalytic olefin hydrogenation using Rh(I) catalyst precursors was studied, and it was found that the observed rates of the reaction differed. The difference in rates can be attributed to the variation in activation energies for the dihydrogen oxidative addition step based on experimental and theoretical studies. Additionally, one of the catalyst precursors rapidly forms an active catalyst, making it impossible to directly compare the rates of hydrogenation.
Article
Chemistry, Multidisciplinary
Daniel P. Zobernig, Michael Luxner, Berthold Stoeger, Luis F. Veiros, Karl Kirchner
Summary: Efficient hydrogenation of terminal alkenes using molecular hydrogen as the hydrogen source is achieved with well-defined bench stable Mn(I) complexes containing an N-heterocyclic carbene-based PCP pincer ligand as the catalyst. This reaction is environmentally friendly and economically viable, utilizing an inexpensive and abundantly available non-precious metal catalyst. DFT calculations provide mechanistic insight into the catalytic reaction.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Luomo Li, Gerhard Hilt
Summary: The study found that using InBr3 as a catalyst can achieve regioselective and regiodivergent addition of H-D from regiospecific deuterated dihydroaromatic compounds to a variety of 1,1-di- and trisubstituted alkenes. Compared to previous catalytic processes, InBr3 has a wider applicability, can overcome old restrictions, and successfully transform new types of substrates.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Anne K. Ravn, Nomaan M. Rezayee
Summary: This study investigates a switchable Cp*-iridium catalyst supported by a 1,10-phenanthroline-2,9-diol for the hydrogenation of amides. The catalyst can selectively induce either C-O or C-N bond scission of the amide depending on the reaction conditions. The addition of base can switch the selectivity to favor C-N bond-cleaved products. These studies provide fundamental insights for the rational design of hydrogenation catalysts.
Article
Chemistry, Inorganic & Nuclear
Gyorgy Hanko, Richard Marton, Antal Udvardy, Mihaly Purgel, Agnes Katho, Ferenc Joo, Gabor Papp
Summary: The water-soluble cis,mer-[IrH2Cl(mtppms)3] was an effective catalyst for the reduction of terminal alkynes by hydrogen transfer, with the highest rate observed at pH 3. The reactions exclusively yielded corresponding alkenes as products, with excess mtppms ligand inhibiting the reaction by forming a less active complex. The joint mechanism for both hydrogenation and transfer hydrogenation pathways was suggested based on experimental results and DFT calculations.
INORGANICA CHIMICA ACTA
(2021)
Article
Chemistry, Multidisciplinary
Manar M. Shoshani, Volodymyr Semeniuchenko, Samuel A. Johnson
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Physical
Mehdi Shakourian-Fard, S. Maryamdokht Taimoory, Volodymyr Semeniuchenko, Ganesh Kamath, John F. Trant
JOURNAL OF MOLECULAR LIQUIDS
(2018)
Article
Chemistry, Applied
Volodymyr Semeniuchenko, Thomas E. Exner, Volodymyr Khilya, Ulrich Groth
APPLIED ORGANOMETALLIC CHEMISTRY
(2011)
Article
Chemistry, Organic
Mostafa Kiamehr, Firouz Matloubi Moghaddam, Satenik Mkrtchyan, Volodymyr Semeniuchenko, Linda Supe, Alexander Villinger, Peter Langer, Viktor O. Iaroshenko
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Volodymyr Semeniuchenko, Ulrich Groth, Volodymyr Khilya
CURRENT ORGANIC SYNTHESIS
(2010)
Article
Chemistry, Multidisciplinary
Volodymyr Semeniuchenko, Yana Garazd, Myroslav Garazd, Tetyana Shokol, Ulrich Groth, Volodymyr Khilya
MONATSHEFTE FUR CHEMIE
(2009)
Article
Chemistry, Organic
Viktor O. Iaroshenko, Iftikhar Ali, Satenik Mkrtchyan, Volodymyr Semeniuchenko, Dmytro Ostrovskyi, Peter Langer
Article
Chemistry, Organic
Mostafa Kiamehr, Firouz Matloubi Moghaddam, Pavel V. Gormay, Volodymyr Semeniuchenko, Alexander Villinger, Peter Langer, Viktor O. Iaroshenko
Article
Chemistry, Organic
Viktor O. Iaroshenko, Sajid Ali, Satenik Mkrtchyan, Ashot Gevorgyan, Tariq Mahmood Babar, Volodymyr Semeniuchenko, Zahid Hassan, Alexander Villinger, Peter Langer
TETRAHEDRON LETTERS
(2012)
Article
Chemistry, Organic
Mostafa Kiamehr, Firouz Matloubi Moghaddam, Volodymyr Semeniuchenko, Alexander Villinger, Peter Langer, Viktor O. Iaroshenko
TETRAHEDRON LETTERS
(2013)
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, 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)
