Article
Chemistry, Multidisciplinary
Han-Jun Ai, Benedict N. Leidecker, Phong Dam, Christoph Kubis, Jabor Rabeah, Xiao-Feng Wu
Summary: Transition metal-catalyzed carbonylative cross-coupling reactions are widely used methods in organic synthesis. However, the practical application of iron as a catalyst in carbonylation reactions has not been extensively explored. Recent studies have shown that iron catalysts can catalyze alkoxycarbonylation reactions and activate alkyl bromides and alkyl iodides through distinct electron transfer processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Peng Wang, Ji Yang, Kangkang Sun, Helfried Neumann, Matthias Beller
Summary: The direct palladium-catalyzed selective carbonylative coupling of less reactive aryl chlorides with primary and secondary amines is achieved using a palladium/Xantphos catalyst system and cesium chloride as an additive. This reaction shows high conversion for various aryl chlorides and good functional group compatibility.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Lars J. Wesenberg, Alessandra Sivo, Gianvito Vile, Timothy Noel
Summary: In recent years, there has been a trend in the synthetic community to introduce sp(3)-carbon-based fragments in organic compounds through cross-coupling strategies. This study presents a novel nickel-catalyzed electrochemical methodology for reductive cross-electrophile coupling, using inexpensive amine-derived radical precursors and aryl iodides. The use of electrochemistry as a power source reduces waste and avoids chemical reductants, making this approach a more sustainable alternative to traditional cross-coupling methods.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dan Li, Li Wei, Chaorong Qi, Wenfang Xiong, Hongjian Liu, Huanfeng Jiang
Summary: A palladium-catalyzed direct carbonylation of aryl bromides with carbon dioxide as the carbonyl source has been developed, providing an efficient route to a variety of aryl carboxylic acids in moderate to high yields. The method has many advantages including the use of a simple palladium catalyst system, wide substrate scope, good functional group tolerance, high yields, and easy scalability.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Yuan Yang, Dilver Pena Fuentes, Xiao-Feng Wu
Summary: Carbonylation reactions are important in contemporary organic chemistry as they provide access to compounds with carbon monoxide or methyl groups. We report a copper-catalyzed carbonylative catenation and borylation reaction and propose a possible reaction mechanism.
Article
Chemistry, Organic
Peizhuo Lv, Ali Wang, Xin Xie, Yulong Chen, Yuanhong Liu
Summary: An efficient method for the coupling of allyl trifluoroborates with aryl halides has been developed. The method offers high efficiency, mild reaction conditions, wide substrate scope, and functional group compatibility. Mechanistic studies suggest the formation of a pi-allyl nickel(III) intermediate as a key reaction intermediate.
Article
Chemistry, Physical
Tanuja Tewari, Rohit Kumar, Samir H. Chikkali
Summary: This study reports the use of an iron catalyst in carbonylation reactions to convert alkynes to alpha,beta-unsaturated esters. The reaction is operationally simple and allows the synthesis of various unsaturated esters.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Physical
Tanuja Tewari, Rohit Kumar, Samir H. Chikkali
Summary: An iron catalyst is reported for the hydroalkoxycarbonylation of alkynes in the presence of CO, affording α,β-unsaturated esters. The reaction is operationally simple and tolerates various functional groups, offering facile access to a range of compounds.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Ryota Isshiki, Miki B. Kurosawa, Kei Muto, Junichiro Yamaguchi
Summary: A Ni-catalyzed aryl sulfide synthesis method was developed using 2-pyridyl sulfide as the sulfide donor, eliminating the need for odorous and toxic thiols. The Ni/dcypt catalyst played a crucial role in the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, with mechanistic studies showing its ability to undergo oxidative additions and ligand exchanges simultaneously.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Letter
Chemistry, Organic
Panchi Guo, Hao Jin, Jinhui Han, Liang Xu, Pengfei Li, Miao Zhan
Summary: This study demonstrates a nickel-catalyzed Negishi cross-coupling reaction for the synthesis of versatile organoboron products with high functional-group tolerance. The reaction allows for the coupling of unactivated tertiary alkyl electrophiles with boron-stabilized organozinc reagents. The importance of the Bpin group in accessing the quaternary carbon center is highlighted, and the practicality of the prepared quaternary organoboronates is showcased through their conversion to other useful compounds.
Article
Chemistry, Multidisciplinary
Zijian Li, Wenxuan Sun, Xianxu Wang, Luyang Li, Yong Zhang, Chao Li
Summary: This method utilizes alcohols and aryl bromides as coupling partners, combining anodic preparation and nickel catalysis to efficiently construct C(sp(2))-C(sp(3)) bonds. The nickel-catalyzed paired electrolysis reaction showcases a broad substrate scope suitable for the synthesis of multifunctional compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Ding Liu, Miaolin Ke, Tong Ru, Yingtang Ning, Fen-Er Chen
Summary: Through systematic optimization of ligand structures and reaction conditions, we successfully report a room-temperature Pd-catalyzed methoxy-carbonylation with high branched selectivity. The strategic design of the new class of bisphosphine-picolinamide ligands enabled the synthesis of various alpha-substituted acrylates in good to excellent yields.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Guo-Qin Hu, Wen-Yan Zhang, Yong-Xin Liu, Jing-Hui Liu, Bin Zhao
Summary: Here, we present a decarboxylative thiocarbonylation method of aryl and alkenyl sulfonium salts using oxalic acid monothioethers (OAMs) under visible light-accelerated palladium catalysis. The reaction demonstrates a new application of visible light-accelerated palladium catalysis in catalytic decarboxylative cross-couplings, allowing the synthesis of different types of thioester compounds. Both sulfonium salts and OAMs are easily accessible and stored reagents.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Pierre-Louis Lagueux-Tremblay, Celestin Augereau, Pranav Nair, Kwan Ming Tam, Bruce A. Arndtsen
Summary: The use of metal catalysis to form potent acylating agents is an important method to broaden the applicability of carbonylation reactions. However, the reductive elimination of these reactive products has presented a challenge, making the reactions often high temperature and high pressure, and limited in scope. In this study, a mild and versatile palladium catalyzed carbonylative method was developed to generate electrophilic acyl-DMAP salts. The use of triflate anion as a counterion destabilizes Pd(II) and allows for irreversible reductive elimination, while ligand design enables the rapid activation of aryl or vinyl triflates.
Article
Chemistry, Physical
Pierre-Louis Lagueux-Tremblay, Celestin Augereau, Pranav Nair, Kwan Ming Tam, Bruce A. Arndtsen
Summary: The use of metal catalysis to form potent acylating agents is an important approach to expand the application of carbonylation reactions. However, the reductive elimination of these reactive products has been a challenge, making these reactions often high temperature, high pressure, and limited in scope. In this study, a mild and versatile palladium catalyzed carbonylative method was developed to generate electrophilic acyl-DMAP salts by exploiting the counterion. The weakly coordinating triflate anion was found to destabilize Pd(II) and enable irreversible reductive elimination, while ligand design facilitated the rapid activation of aryl or vinyl triflates. This approach allows palladium catalyzed carbonylations to be carried out under exceptionally mild conditions, with low catalyst loading and using readily available C(sp2)-triflate reagents.
Article
Biochemical Research Methods
Karoline T. Neumann, Anders T. Lindhardt, Benny Bang-Andersen, Troels Skrydstrup
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
(2017)
Article
Chemistry, Applied
Rasmus K. Jensen, Nikolaj Thykier, Martin V. Enevoldsen, Anders T. Lindhardt
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2017)
Article
Chemistry, Multidisciplinary
Steffan K. Kristensen, Espen Z. Eikeland, Esben Taarning, Anders T. Lindhardt, Troels Skrydstrup
Article
Chemistry, Multidisciplinary
M. B. Johansen, A. T. Lindhardt
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Zhuo Xin, Jiahui Zhang, Katerina Sordakis, Matthias Beller, Chen-Xia Du, Gabor Laurenczy, Yuehui Li
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)
Editorial Material
Chemistry, Multidisciplinary
Zhuo Xin, Troels Skrydstrup
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Zhuo Xin, Le Jia, Yuxing Huang, Chen-Xia Du, Yuehui Li
Article
Chemistry, Physical
Jiaying Yu, Yunshuo Yang, Runtao Jia, Kim Daasbjerg, Jun Wang, Mauro Carraro, Zhuo Xin, Yuxing Huang, Troels Skrydstrup
APPLIED SURFACE SCIENCE
(2020)
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
Martin V. Enevoldsen, Jacob Overgaard, Maja S. Pedersen, Anders T. Lindhardt
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Yuxing Huang, Zhuo Xin, Wenlong Yao, Qi Hu, Zhuohua Li, Liuqing Xiao, Bo Yang, Junmin Zhang
CHEMICAL COMMUNICATIONS
(2018)
