Article
Chemistry, Multidisciplinary
Craig S. S. Day, Stephanie J. J. Ton, Clemens Kaussler, Daniel Vronning Hoffmann, Troels Skrydstrup
Summary: Here, a methodology for accessing isotopically labeled esters and amides from carbonates and carbamates utilizing an oxygen deletion strategy is reported. The methodology employs a decarboxylative carbonylation approach using C-12 or C-13 carbon monoxide generated ex situ in near stoichiometric amounts for isotope labeling. The reaction demonstrates a broad scope, functional group tolerance, and high yields, exemplified by the synthesis of structurally complex molecules. Additionally, a complementary method for the catalytic in situ generation of CO from CO2 liberated during decarboxylation is developed as a proof-of-concept approach for converting CO2-derived compounds to CO-containing frameworks. Mechanistic studies provide insights into the catalytic steps and the impact of ligand choice for overcoming challenges in low-pressure carbonylation methodologies, aiding the development of future methodologies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Fanni Bede, Laszlo Kollar, Nandor Lambert, Peter Huszthy, Peter Pongracz
Summary: Palladium-catalyzed hydroaminocarbonylation reactions of olefins using aliphatic amines were successfully performed under carbon monoxide atmosphere. The targeted amides were synthesized in moderate to good isolated yields without the need for acidic additives. The effect of chiral diphosphines on product distribution, including chemo-, regio-, and enantioselectivities, was also investigated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Beata Gatlik, Wojciech Chaladaj
Summary: A Pd-catalyzed three-component protocol was developed for the direct synthesis of perfluoroalkyl-substituted alpha,beta-unsaturated esters using formates as convenient CO sources. The reaction proceeded smoothly under mild conditions with high yields and excellent selectivities. Detailed mechanistic studies supported by DFT calculations were conducted to understand the reaction pathway.
Article
Chemistry, Multidisciplinary
Taichi Kusakabe, Dongwei Liu, Kaori Tsuchida, Shun Okazaki, Tsuyoshi Hashimoto, Akane Mori, Kentaro Yoshiwaka, Hiroaki Sasai, Keisuke Takahashi, Keisuke Kato
Summary: The palladium-catalyzed methoxy-methoxycarbonylation of monosubstituted allenes was reexamined. It was found that arylallenes provided methyl 2-methoxymethylacrylates in good yield with moderate to good enantioselectivity, while alkylallenes afforded methyl 2-methoxymethylacrylates regioselectively but with low enantioselectivity.
Article
Chemistry, Multidisciplinary
Yao Ge, Fei Ye, Ji Yang, Anke Spannenberg, Haijun Jiao, Ralf Jackstell, Matthias Beller
Summary: A novel palladium-catalyzed cascade carbonylation is described for the direct and selective synthesis of alpha,beta-unsaturated piperidones, generating a broad range of intriguing heterocycles from easily available propargylic alcohols and aliphatic amines. The success of this transformation hinges on the catalytic cleavage of the carbon-carbon triple bond by a specific catalyst with 2-diphenylphosphinopyridine as ligand and suitable reaction conditions, with mechanistic studies pointing to the importance of branched unsaturated acid 11 as a crucial intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Diego Olivieri, Riccardo Tarroni, Stefano Zacchini, Nicola Della Ca', Raffaella Mancuso, Bartolo Gabriele, Gilberto Spadoni, Carla Carfagna
Summary: The direct alkoxy-aryloxycarbonylation reaction of olefins has been achieved for the first time, leading to the formation of mixed alkyl aryl succinates. The reaction shows high regioselectivity and moderate to excellent yields. Detailed DFT calculations and experimental results support the proposed catalytic cycle, which involves the crucial role of p-benzoquinone as both regenerating the active species and promoting the final elimination step.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Csaba Arvai, Laszlo T. Mika
Summary: This review summarizes the recent applications of alternative solvents in improving the efficiency, safety, and environmental friendliness of carbonylation reactions. The use of water, biomass-based alcohols, ionic liquids, and other alternative solvents can enhance the reaction protocols.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Louise Ponsard, Emmanuel Nicolas, Ngoc Huan Tran, Sarah Lamaison, David Wakerley, Thibault Cantat, Marc Fontecave
Summary: A system coupling high-pressure CO2 electrolysis with thermal catalysis using high-pressure CO has been developed to convert CO2 into beta-butyrolactone, achieving a high reaction yield. This strategy enables the production of lactones from CO2 for polyester synthesis, expanding the range of chemicals derived from CO2.
Article
Chemistry, Physical
Roushan Prakash Singh, Soumen Sinhababu, Neal P. Mankad
Summary: This Perspective reviews recent advances and applications of Al/M heterobimetallic catalysis in various areas, including polymerization, epoxide activation and carbonylation. The mechanistic role of the aluminum site is highlighted, and a comprehensive perspective is constructed by including a broad range of Al-containing metalloligands and Al/M combinations.
Article
Chemistry, Multidisciplinary
Xiaolei Ji, Chaoren Shen, Xinxin Tian, Hongru Zhang, Xinyi Ren, Kaiwu Dong
Summary: In this study, a Pd-catalyzed asymmetric double hydroxycarbonylation of terminal alkynes was developed using relay catalysis, which provided an efficient route to chiral succinic acids. This method demonstrated high yields and enantioselectivity for 41 examples and showcased its synthetic utilities in the facile synthesis of key intermediates for chiral pharmaceuticals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Ida Ziccarelli, Raffaella Mancuso, Francesco Giacalone, Carla Calabrese, Valeria La Parola, Alex De Salvo, Nicola Della Ca', Michelangelo Gruttadauria, Bartolo Gabriele
Summary: This article reports the successful heterogenization of the classical PdI(4)(2-)carbonylation catalyst on multi-walled carbon nanotubes. The newly developed heterogeneous catalyst shows good activity and recyclability in the oxidative monoaminocarbonylation reaction, with limited metal contamination in the final organic compounds.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
James E. Baumann, Gojko Lalic
Summary: A new method for the differential dihydrofunctionalization of terminal alkynes has been developed, enabling the synthesis of allylic boronate esters through a reductive three-component coupling reaction. This transformation, promoted by a copper/palladium catalyst system, hydrofunctionalizes both pi-bonds of the alkyne. The method is compatible with a wide range of functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Ding Ma, Chenyang Wang, Deshen Kong, Yongliang Tu, Peng Shi, Carsten Bolm
Summary: Palladium-catalyzed carbonylation reactions with Cr(CO)(6) as carbonyl source are key for the preparation of N-ynonylsulfoximines from NH-sulfoximines and bromoalkynes, affording the corresponding products in good yields at room temperature with a wide range of substrate combinations.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Simon Sieger, Ilja Lubins, Bernhard Breit
Summary: A highly versatile palladium-catalyzed allylation reaction has been reported, providing a waste-free access to allylated nucleophiles with unlimited possibilities for further functionalization. The reaction can be conducted using propadiene in toluene, and the mechanism is supported by deuterium labeling experiments.
Article
Chemistry, Physical
Simon V. Sieger, Ilja Lubins, Bernhard Breit
Summary: A highly versatile palladium-catalyzed allylation reaction using various pronucleophiles has been reported. Through the use of propadiene in toluene, this reaction provides an efficient and waste-free method to obtain allylated nucleophiles with unlimited potential for further functionalization. The Pd/BINAP system is not only capable of adding N-, O-, and S-pronucleophiles, but also C-pronucleophiles to allene. The plausible mechanism is supported by deuterium labeling experiments.
Article
Biochemical Research Methods
Karoline T. Neumann, Anders T. Lindhardt, Benny Bang-Andersen, Troels Skrydstrup
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
(2017)
Article
Chemistry, Organic
Hongfei Yin, Troels Skrydstrup
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Anna Skogh, Stig D. Friis, Troels Skrydstrup, Anja Sandstrom
Article
Chemistry, Inorganic & Nuclear
Thomas L. Andersen, Soren Kramer, Jacob Overgaard, Troels Skrydstrup
Article
Chemistry, Organic
Mathias Flinker, Sara Lopez, Dennis U. Nielsen, Kim Daasbjerg, Frank Jensen, Troels Skrydstrup
Article
Chemistry, Multidisciplinary
Steffan K. Kristensen, Espen Z. Eikeland, Esben Taarning, Anders T. Lindhardt, Troels Skrydstrup
Article
Chemistry, Physical
Martin Juhl, Simon L. R. Laursen, Yuxing Huang, Dennis U. Nielsen, Kim Daasbjerg, Troels Skrydstrup
Article
Chemistry, Multidisciplinary
M. B. Johansen, A. T. Lindhardt
CHEMICAL COMMUNICATIONS
(2018)
Review
Biochemical Research Methods
Dennis U. Nielsen, Karoline T. Neumann, Anders T. Lindhardt, Troels Skrydstrup
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
(2018)
Article
Chemistry, Applied
Martin B. Johansen, Jens C. Kondrup, Mogens Hinge, Anders T. Lindhardt
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2018)
Article
Chemistry, Applied
Rasmus A. T. Verdier, Jesper H. Mikkelsen, Anders T. Lindhardt
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2018)
Article
Chemistry, Organic
Martin B. Johansen, Anders T. Lindhardt
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Xin-Ming Hu, Magnus H. Ronne, Steen U. Pedersen, Troels Skrydstrup, Kim Daasbjerg
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Thomas L. Andersen, Patrik Nordeman, Heidi F. Christoffersen, Helene Audrain, Gunnar Antoni, Troels Skrydstrup
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Martin V. Enevoldsen, Jacob Overgaard, Maja S. Pedersen, Anders T. Lindhardt
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
