Article
Chemistry, Multidisciplinary
Ryota Sato, Tomoki Lida, Takaki Kanbara, Junpei Kuwabara
Summary: This Pd-catalysed cross-dehydrogenative coupling reaction allows the introduction of two polyfluoroarenes into simple polyaromatic hydrocarbons at sterically favourable positions. The investigation of the reaction mechanism revealed that the unique regioselectivity is determined by the reductive elimination step rather than the C-H bond cleavage step.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Andreas Hess, Jan P. Prohaska, Sabrina B. Doerrich, Florian Trauner, Ferdinand H. Lutter, Sebastien Lemaire, Simon Wagschal, Konstantin Karaghiosoff, Paul Knochel
Summary: A new toluene-soluble reagent, sBu(2)Mg, has been developed for regioselective ortho-magnesiations of various N-arylated pyrazoles and 1,2,3-triazoles, as well as arenes with specific directing groups. The resulting diarylmagnesium reagents can be further functionalized and double ortho,ortho'-magnesiations can be achieved by repeating the magnesiation/electrophile trapping sequence, allowing for the preparation of valuable functionalized arenes.
Article
Chemistry, Multidisciplinary
Balazs L. Toth, Anna Monory, Orsolya Egyed, Attila Domjan, Attila Benyei, Balint Szathury, Zoltan Novak, Andras Stirling
Summary: The study introduces a substrate-only-based model to interpret the influence of neighboring groups on the directing group in ortho-C-H bond activation reactions, defining the Ortho Effect (OE) for such situations. Simple descriptors like torsion angle and torsional energy are used to predict and explain substrate reactivity in directed C-H activation reactions. Structural and energetic criteria are set to evaluate the efficiency of the metalation step, providing guidance for organic chemists and predictions for reaction conditions for selected directing groups.
Article
Chemistry, Physical
Avishek Das, Nitin T. Patil
Summary: A ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction between aryl iodides and aliphatic alcohols is reported. The method is demonstrated to be useful for the synthesis of various aryl alkyl ethers, including complex biomolecules and medicinally relevant motifs. The importance of gold catalysis is highlighted in overcoming selectivity issues observed with other transition metal catalysts in C-O cross -coupling reactions.
Article
Chemistry, Physical
Avishek Das, Nitin T. Patil
Summary: Reported in this study is a ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction between aryl iodides and aliphatic alcohols. The usefulness of the method is demonstrated by successfully synthesizing a variety of aryl alkyl ethers, including complex biomolecules and medicinally relevant motifs. The importance of gold catalysis is highlighted by overcoming the selectivity issues commonly observed when other transition metals are used as catalysts for C-O cross-coupling reactions.
Article
Chemistry, Physical
Kaituo Dong, Cristofer Pezzetta, Qiu-Cheng Chen, Alexander Kaushansky, Amedeo Agosti, Giacomo Bergamini, Robert Davidson, Lilac Amirav
Summary: Carbon-heteroatom cross-coupling reactions are important for industrial chemical processes, especially for the synthesis of pharmaceuticals, agrochemicals, and biologically active compounds. Photocatalyst/transition metal dual catalytic systems, using semiconductor nanoparticles as heterogeneous light sensitizers, offer advantages such as low-cost production, tunable photophysical properties, easy separation, high photostability, and recyclability. The combination of CdSe@CdS nanorod photocatalysts with a Ni complex catalyst enables efficient selective light-induced C-O cross-coupling reactions, achieving high yield and impressive turnover numbers.
Article
Chemistry, Multidisciplinary
Jin Tanaka, Yuki Nagashima, Antonio Junio Araujo Dias, Ken Tanaka
Summary: A novel photoinduced in situ reduction reaction of half-sandwich metal [Rh(III)] complexes to low-valent anionic metal [Rh(II)] ate complexes has been reported, enabling room temperature ortho-C-H borylation of arenes. This strategy was facilitated by using a functionalized cyclopentadienyl (Cp-A3) Rh(III) catalyst developed by the researchers.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Jagriti Chaturvedi, Chabush Haldar, Ranjana Bisht, Gajanan Pandey, Buddhadeb Chattopadhyay
Summary: An electrostatically directed meta borylation method allows for highly selective borylation reactions on various substrates. This method avoids the need to synthesize complex ligands/templates and can be conducted under milder conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Ping-Shan Lai, Ross D. Jansen-van Vuuren, Robert P. Lemieux, Victor Snieckus
Summary: Two new smectic C* mesogens were synthesized using a complex synthetic strategy, with one forming a nematic phase and the other forming a smectic A phase. The wide temperature range of the smectic phase for one of the mesogens suggests stabilization of the mesophase by intermolecular hydrogen bonding.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shyam Kumar Banjare, Tanmayee Nanda, Bedadyuti Vedvyas Pati, Pragati Biswal, Ponneri Chandrababu Ravikumar
Summary: This review highlights recent advances in cobalt-catalysed C-H functionalization, emphasizing the use of oxygen atom coordination for sustainable synthesis. While nitrogen-directed functionalizations are well explored, the use of oxygen as a weakly coordinating atom for C-H activation remains largely underdeveloped. The application of cobalt and weakly coordinating directing groups, such as oxygen, shows promise for selective C-H functionalization reactions in the pharmaceutical industry, with potential for further development beyond C-C and C-N bond formation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Mimi Xing, Huanhuan Cui, Chun Zhang
Summary: A novel nickel-catalyzed reductive cross-coupling method has been developed for constructing C-Si bonds under mild reaction conditions, allowing for the synthesis of structurally diverse organosilanes without Ni-catalyzed isomerization. The utility of this chemistry is demonstrated through further transformations of the product, while the radical mechanism of the reaction is elucidated through control experiments.
Article
Chemistry, Organic
Jiao Jiao, Wenzheng Nie, Peidong Song, Pengfei Li
Summary: A new air-stable Si,S-chelating ligand has been developed and successfully utilized in iridium-catalyzed ortho C-H borylation reaction with a broad substrate scope, providing a rapid, efficient, and economic method for the preparation of organoboron compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Organic
C. M. A. Afsina, Thaipparambil Aneeja, Mohan Neetha, Gopinathan Anilkumar
Summary: Copper-catalyzed organic reactions have attracted widespread attention due to the abundance and affordability of copper, as well as its low toxicity, eco-friendliness, sustainable nature, and versatility as a catalyst. These reactions are primarily used for the synthesis of biologically important nitrogen heterocycles, amines, amides, imines, and alkynes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Sangeeta Kumari, Charu Sharma, Naveen Satrawala, Avinash K. Srivastava, Kamal N. Sharma, Raj K. Joshi
Summary: In this study, a novel reaction methodology utilizing selenium as a directing group was developed for the synthesis of compounds containing benzyl selenide functional group. The method is simple and efficient, and selenium is a commonly used laboratory reagent.
Article
Chemistry, Multidisciplinary
Ayan Jati, Suranjana Dam, Shekhar Kumar, Kundan Kumar, Biplab Maji
Summary: Researchers synthesized a pyrene-based two-dimensional C=C linked pi-conjugated COF with Ni(ii)-centers through bipyridine moieties. This COF catalyst exhibited significantly higher efficiencies in diverse photocatalytic C-X cross-coupling reactions compared to homogeneous controls, due to enhanced energy and electron transfer.
Article
Chemistry, Multidisciplinary
Sebastian Sandl, Axel Jacobi von Wangelin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Michael Neumeier, Uttam Chakraborty, Dieter Schaarschmidt, Victor de la Pena O'Shea, Raul Perez-Ruiz, Axel Jacobi von Wangelin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Luana Cardinale, Mikhail O. Konev, Axel Jacobi von Wangelin
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Editorial Material
Chemistry, Multidisciplinary
Thomas M. Maier, Sebastian Sandl, Peter Melzl, Josef Zweck, Axel Jacobi von Wangelin, Robert Wolf
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Luana Cardinale, Michael Neumeier, Michal Majek, Axel Jacobi von Wangelin
Article
Chemistry, Multidisciplinary
Pradip Ghosh, Axel Jacobi von Wangelin
Summary: The reductive transformations of easily available oxidized matter play a crucial role in synthetic manipulation and chemical valorization. The use of liquid reducing agents and simple setups in catalytic hydrofunctionalization adds to its practicality. Metal-catalyzed hydroborations offer a productive platform for reductive valorizations of stable C=X electrophiles, as demonstrated in this study with the pre-catalyst Mn(hmds)(2) for the reduction of various functional groups under mild conditions, including successful depolymerizations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Pradip Ghosh, Roland Schoch, Matthias Bauer, Axel Jacobi von Wangelin
Summary: Metal-catalyzed C-H activation is an environmentally friendly and economically attractive synthetic strategy, which can reduce waste generation and reveal a tandem catalysis mechanism through a series of mechanistic studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Luana Cardinale, Mattis-Ole W. S. Schmotz, Mikhail O. Konev, Axel Jacobi von Wangelin
Summary: The study presents a straightforward protocol for the photocatalytic carbamoylation of imines using easily accessible and stable 4-amido Hantzsch ester derivatives as precursors to carbamoyl radicals. The reaction occurs under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and acid additives, with mechanistic studies suggesting a photoredox mechanism involving carbamoyl radicals.
Article
Chemistry, Inorganic & Nuclear
Andrey Fedulin, Sandeep K. Gupta, Isabelle Ruter, Franc Meyer, Axel Jacobi von Wangelin
Summary: The combination of pyridonate ligands with transition metal ions allows the synthesis of diverse coordination compounds. This study synthesized novel Fe5 and Fe4 clusters, with Fe5 cluster exhibiting a diamondoid structure and Fe4 cluster showing a butterfly motif. Magnetic tests revealed the rare single-molecule magnet behavior of Fe4 cluster.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ursula Rastetter, Axel Jacobi von Wangelin, Carmen Herrmann
Summary: To improve the catalytic activity of 3d transition metal catalysts, the use of redox-active ligands is promising. First-principles calculations, specifically density functional theory with a proper choice of exchange-correlation functional, are crucial for studying these ligands' influence on the electronic properties of metal complexes. Tests on a class of metal complexes showed that the spin-state energy splittings depend linearly on the amount of exact exchange included in the calculations. The sensitivity of the spin-state energetics to the exact exchange is surprisingly small, despite the significant impact of varying redox-activity on the electronic structure of the complexes.
JOURNAL OF COMPUTATIONAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sarah Kirchhecker, Ngoc Nguyen, Stefan Reichert, Karola Luetzow, Paul Eselem S. Bungu, Axel Jacobi von Wangelin, Sebastian Sandl, Axel T. Neffe
Summary: The combination of inexpensive Fe(ii) acetate with low molecular weight aliphatic carboxamides in situ generates an effective catalyst system for the ring opening polymerisation of lactones. PLLAs with high molar masses, narrow dispersity, and without racemisation were successfully produced. Furthermore, the synthesis of PLLA-PCL block copolymers with low randomness was achieved. This catalyst mixture has the potential to be used in polymers with biomedical applications.
Review
Chemistry, Physical
Andrey Fedulin, Axel Jacobi von Wangelin
Summary: Aminoalcohols are a readily available, highly diverse, and inexpensive class of ligands. Among them, 2-pyridonates exhibit particularly intriguing stereoelectronic features and have been applied to various coordination chemistry reactions. Transition metal complexes with pyridonate ligands have been developed for powerful catalytic transformations.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Review
Chemistry, Physical
Dominik Gaertner, Sebastian Sandl, Axel Jacobi von Wangelin
CATALYSIS SCIENCE & TECHNOLOGY
(2020)
Article
Chemistry, Multidisciplinary
Patrick Bayer, Axel Jacobi von Wangelin
Article
Chemistry, Organic
Pradip Ghosh, Axel Jacobi von Wangelin
ORGANIC CHEMISTRY FRONTIERS
(2020)