Article
Chemistry, Physical
Jordan L. Harper, Stephanie Felten, Ryan M. Stolley, Alexander S. Hegg, Paul H-Y Cheong, Janis Louie
Summary: The mechanistic investigation into the origins of regio- and chemoselectivities observed in iron/pyridine dialdimine (PDAI)-catalyzed intermolecular [2+2+2] cycloaddition reactions of terminal alkynes and cyanamides reveals the significant role of the hemilabile PDAI ligand in controlling the observed selectivity of the resultant products.
Article
Chemistry, Multidisciplinary
Callum R. Woof, Derek J. Durand, Ruth L. Webster
Summary: An iron(II)-catalyzed polymerization of arylallenes has been reported, generating high molecular weight polymers at room temperature. The polymer structures and chain lengths of various monomers were determined using NMR, DSC, and GPC analysis. Mechanistically, it is proposed that chain growth occurs through a reactive Fe(III) species, rather than the formation of an iron(II) hydride in situ.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Cheng Niu, Da-Ming Du
Summary: A new protocol for accessing CF3-containing bispiro[isoquinolone-pyrrolidine-benzothiophenone]s has been described. A series of 1,3-dipoles were synthesized from isoquinolinetrione and CF3CH2NH2, and the 1,3-dipolar cycloaddition of isoquinolinedione trifluoroethyl ketimines and unsaturated benzothiophenones in the presence of 10 mol% DABCO delivered the corresponding adducts with excellent yields (up to 98%) and diastereoselectivities (up to >20 : 1 dr).
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Morgane de Robichon, Thilo Kratz, Frederike Beyer, Julian Zuber, Christian Merten, Thorsten Bach
Summary: Substituted bicyclo[1.1.0]butanes add enantioselectively to 2(1H)-quinolones upon irradiation, leading to the formation of products with a chiral bicyclo[2.1.1]hexane skeleton. A two-point hydrogen bond between the quinolone and the template is responsible for stereocontrol in the photocycloaddition reaction. The chiral template can be recovered and reused, and sensitization is a suitable tool for performing the reaction with visible light.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Shuo Sun, Yabo Deng, Danna Chen, Hai Guo, Mengmeng Sun, Honghua He, Wenjin Yan, Jinqi Huang
Summary: We present a directly catalytic asymmetric method for the synthesis of CF2H-containing pyrrolidines. A range of enantioenriched difluoromethylated pyrrolidine (34 examples, up to 97% ee) were obtained using a 1,3-dipole cycloaddition model. The subsequent hydrolysis reaction yielded a new difluoromethyl substituted fused ring compound with potential anticancer activity.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Vipin Singh, Shanta Raj Lakshmi, L. Raju Chowhan
Summary: In this study, a short and efficient method for synthesizing novel polyheterocyclic chromeno spiro-pyrrolidine oxindoles via 1,3-dipolar cycloaddition reaction mediated by graphene oxide (GO) catalyst was reported. The method showed high yields and green synthetic approach, with the catalyst having a low loading and no formation of side products. The products were easily isolated without the use of any chromatographic techniques.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Zheng-Jun Chen, Wei Liang, Zhuo Chen, Lin Chen
Summary: An efficient and practical 1,3-dipolar [3+2] cycloaddition of N-2,2,2-trifluoroethylisatin ketimines and maleimides has been achieved through phase-transfer catalytic process using a cheap quaternary ammonium salt as a catalyst. The reaction results in the rapid generation of complex trifluoromethyl spiro-fused compounds in good yields and with excellent diastereoselectivities. The investigation on the reaction mechanism suggests that tetrahexylammonium carbonate might be the real catalyst in the cycloaddition process.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Amit Singh Adhikari, Soumen Pandit, Ruchir Kant, Nilanjana Majumdar
Summary: An efficient method for highly selective allylic substitution of vinylcyclopropanes using carboxylic acids via iridium catalysis has been developed, providing a high yield of synthetically useful chiral building blocks. The practical application of the products in useful transformations demonstrates its utility.
Article
Chemistry, Inorganic & Nuclear
Mae Feo, Faycel Djebbar, Fedor Zhurkin, Laurent Binet, Nadia Touati, Matthew C. Leech, Kevin Lam, Eric Bremand, Guillaume Lefevre
Summary: In this work, we study the spectroscopic and reactivity properties of a non-innocent paramagnetic iron complex (bcp & BULL;-)2FeII. The complex features a Fe0 center stabilized by two bathocuproine (bcp) ligands. DFT calculations reveal that the paramagnetic 1H NMR behavior of the complex arises from the contribution of two electronic states. The complex exhibits strong anti-ferromagnetic coupling and can activate alkynes in catalytic cycloadditions.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yanyao Liu, M. Kevin Brown
Summary: A strategy utilizing temporary ring constraint to achieve photosensitized [2 + 2] cycloadditions is reported. This strategy overcomes challenges with the cycloaddition of acyclic substrates and has been demonstrated in the synthesis of valuable heterocycles and biatriosporin D.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Xin Chang, Xiang Cheng, Chun-Jiang Wang
Summary: This article introduces an efficient method for synthesizing pharmaceutical compounds with deuterium labels, which addresses the challenge of building deuterium-containing stereogenic centers in organic synthesis. By combining H/D exchange and 1,3-dipolar cycloaddition in a catalytic asymmetric strategy, bioactive alpha-deuterated pyrrolidine derivatives were constructed with high yields and excellent stereoselectivities.
Article
Chemistry, Multidisciplinary
Adriana Luque, Jonathan Gross, Till J. B. Zaehringer, Christoph Kerzig, Till Opatz
Summary: This article describes the first intermolecular visible light [3+2] cycloaddition reaction using acetylenic sulfones on a meta photocycloadduct. The developed methodology combines UV and visible light in a two-step sequence to generate a photo-generated cyclopropane, which then undergoes a strain-release process to form a new cyclopentane ring, significantly increasing the molecular complexity. Mechanistic studies and DFT calculations reveal an energy transfer pathway for the visible light-driven reaction step. This strategy could be extended to simpler vinylcyclopropanes.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Yating Dai, Hongchun Huang, Shuangshuang Liang, Yanli Yin, Xu Ban, Xiaowei Zhao, Zhiyong Jiang
Summary: In this study, an enantioselective intermolecular [3 + 2] cycloaddition of N-arylcyclopropylamines with 2-aryl acrylates/ketones and cyclic ketone-derived terminal olefins via asymmetric photoredox catalysis was reported. A dual catalyst system involving DPZ and a chiral phosphoric acid was effective for the transformations, leading to a wide array of valuable cyclopentylamines with high yields, ee's, and drs. Elaborate modulation of the ester group of 2-aryl acrylates was shown to be effective in improving reactivity, thereby enabling the success of the transformations.
Article
Chemistry, Organic
Vitaly V. Shorokhov, Sergey S. Zhokhov, Victor B. Rybakov, Maksim A. Boichenko, Ivan A. Andreev, Nina K. Ratmanova, Igor V. Trushkov, Olga A. Ivanova
Summary: A Lewis acid-promoted domino ring-opening cyclization of readily available donor-acceptor cyclopropanes with a preinstalled electrophilic center, embedded in a donor group, to functionalized 1,2-dihydronaphthalenes is reported. The obtained compounds are transformed to pharmacologically attractive bridged tricyclic esters in a diastereospecific manner.
Article
Chemistry, Physical
Takeshi Yasui, Rine Tatsumi, Yoshihiko Yamamoto
Summary: In this study, a dual cobalt and photoredox catalysis was utilized for the [2+2+2] cycloaddition of enediynes to produce tricyclic cyclohexadienes with a quaternary bridgehead carbon. The use of a chiral ligand, (S)-Segphos, enabled highly enantioselective reactions, leading to highly enantio-enriched cyclohexadienes.
Article
Chemistry, Multidisciplinary
Lei Guo, Bernd Plietker
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Physical
Annika Roeske, Isabel Alt, Bernd Plietker
Article
Chemistry, Multidisciplinary
Pascal Eisele, Franziska Ullwer, Sven Scholz, Bernd Plietker
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Aslihan Baykal, Bernd Plietker
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Applied
Michael Dyballa, Carolin Rieg, Daniel Dittmann, Zheng Li, Michael Buchmeiser, Bernd Plietker, Michael Hunger
MICROPOROUS AND MESOPOROUS MATERIALS
(2020)
Article
Chemistry, Organic
Marie-Idrissa Picher, Bernd Plietker
Article
Chemistry, Inorganic & Nuclear
Manuel Kirchhof, Katrin Gugeler, Felix Richard Fischer, Michal Nowakowski, Alina Bauer, Sonia Alvarez-Barcia, Karina Abitaev, Marc Schnierle, Yaseen Qawasmi, Wolfgang Frey, Angelika Baro, Deven P. Estes, Thomas Sottmann, Mark R. Ringenberg, Bernd Plietker, Matthias Bauer, Johannes Kaestner, Sabine Laschat
Article
Chemistry, Organic
Felix Krupp, Marie-Idrissa Picher, Wolfgang Frey, Bernd Plietker, Clemens Richert
Summary: In this study, the diastereomeric configuration of propargyl cyclopropanes was determined by co-crystallization with 1,3,5,7-tetrakis(2-bromo-4-methoxyphenyl)adamantane, providing a new method to determine the stereochemical configuration of organic molecules that are difficult to crystallize by themselves. This finding expands the scope of co-crystallization with tetraaryladamantanes as a solution to challenging stereochemical analysis in organic synthesis.
Article
Chemistry, Physical
Lukas Huckmann, Sonia Alvarez-Barcia, Marina Fuhrer, Bernd Plietker, Johannes Kaestner
Summary: Amines are a common class of compounds found in various organic building blocks, and hydrogen autotransfer catalysis has emerged as a new concept for their synthesis. A study on secondary amine formation catalyzed by a NNNN(P)Ru-complex reveals the necessity for the ligand to open a coordination site and the significant enhancement of a condensation reaction in the presence of the ruthenium complex. The regeneration of the catalyst is achieved through the back-transfer of the hydride to the substrate.
Article
Chemistry, Physical
Mathis Benedikter, Janis Musso, Manoj K. Kesharwani, K. Leonard Sterz, Iris Elser, Felix Ziegler, Felix Fischer, Bernd Plietker, Wolfgang Frey, Johannes Kaestner, Mario Winkler, Joris van Slageren, Michal Nowakowski, Matthias Bauer, Michael R. Buchmeiser
Article
Chemistry, Multidisciplinary
Sebastian T. Emmerling, Felix Ziegler, Felix R. Fischer, Roland Schoch, Matthias Bauer, Bernd Plietker, Michael R. Buchmeiser, Bettina Lotsch
Summary: Covalent organic frameworks (COFs) offer vast structural and chemical diversity, and have the potential to play a greater role in catalytic reactions. This study demonstrates the alteration of reactions under spatial confinement by immobilizing specific catalysts on COF pore walls. The results show significantly improved selectivity in macrocyclization reactions compared to homogeneous catalysts, along with a substrate-size dependency in selectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Frederik Kramm, Franziska Ullwer, Benedict Klinnert, Min Zheng, Bernd Plietker
Summary: We present an unusual cyclopropyl enyne cycloisomerization that activates C-C bonds in cyclopropanes, leading to the synthesis of substituted non-canonical tricyclic cyclobutanes with high stereocontrol using [(Ph3P)(2)Fe(CO)(NO)]BF4 as catalyst.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Peng Chen, Xiaohan Sun, Tobias Pietsch, Bernd Plietker, Eike Brunner, Michael Ruck
Summary: The commercialization of zinc batteries and capacitors is hindered by the growth of dendrites, limited coulombic efficiency (CE), and the lack of high-voltage electrolytes. These issues are addressed by a new electrolyte based on the zinc(II)-betaine complex [Zn(bet)(2)][NTf2](2). Solutions in acetonitrile (AN) prevent dendrite formation. The zinc-based batteries and capacitors show excellent performance and stability.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Physical
Fabian Rami, Franziska Baechtle, Bernd Plietker
CATALYSIS SCIENCE & TECHNOLOGY
(2020)
Review
Chemistry, Physical
Bernd Plietker, Annika Roeske
CATALYSIS SCIENCE & TECHNOLOGY
(2019)
