Article
Chemistry, Organic
Gowsia Jan, Diksha Rajput, Anish Gupta, Dolma Tsering, Muthu Karuppasamy, Kamal K. Kapoor, Vellaisamy Sridharan
Summary: An efficient catalytic reaction method for the direct synthesis of valuable indolo[3,2-b]carbazole compounds has been reported in this study. The method exhibits high atom- and step-economy, and generates multiple new chemical bonds in a single synthetic operation.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Illia Lenko, Alexander Mamontov, Carole Alayrac, Remi Legay, Bernhard Witulski
Summary: The research demonstrates the divergent Pd-catalyzed reaction cascades with various 1,3-diynamides, leading to different products depending on the presence or absence of TBAF. Furthermore, deuterium labeling experiments reveal the unique formation mechanism of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Jessica Rodriguez, David Vesseur, Alexis Tabey, Sonia Mallet-Ladeira, Karinne Miqueu, Didier Bourissou
Summary: A (MeDalphos)AuCI complex has been discovered to efficiently catalyze the cross-coupling reaction of indoles and allyl acetates/alcohols. The reaction tolerates various functional groups and selectively produces branched C3-allylated products. It utilizes the hemilabile character of the P<^>N ligand.
Article
Chemistry, Organic
Xian-Tao Wu, En-Kai Xiao, Feng Ma, Jin Yin, Jie Wang, Peng Chen, Yi-Jun Jiang
Summary: A general, efficient, and substrate-controlled regiodivergent trifluoroacetylation of carbazoles has been developed through Friedel-Crafts acylation. This method is applicable to a wide range of readily available substituted carbazoles, achieving yields of up to 99%, and illustrates the impact of different substituents on the products. Additionally, this approach enables the synthesis of chlorodifluoroacetylated and pentafluoropropionylated carbazoles for the first time.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
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, Applied
Xin-Hua Peng, Rui Bai, Shanshan Liu, Zhuo Li, Lin-Yu Jiao
Summary: A novel and efficient protocol for the rare-earth metal salt-catalyzed substitution of phosphoryl azides with amines was disclosed. The methodology generated a series of phosphoryl amides, but secondary analogues or anilines were reluctant to undergo desired transformations.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Christoph M. Hendrich, Valentin D. Hannibal, Lukas Eberle, Leif E. Hertwig, Ute Zschieschang, Frank Rominger, Matthias Rudolph, Hagen Klauk, A. Stephen K. Hashmi
Summary: This study presents a gold-catalyzed bidirectional synthesis method for N-heteropolycyclic compounds bearing carbazole moieties, resulting in the synthesis of four previously unknown core structures. The approach is convergent and modular, with a key step involving a gold-catalyzed cascade reaction starting from stable di-azido compounds. The synthesized molecules were fully characterized, and their optical and electronic properties, as well as their performance in organic thin-film transistors generated by vacuum deposition, were studied, with charge-carrier mobilities of up to 0.3 cm(2)/Vs measured.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Jiajun Wu, Satawat Tongdee, Yuvaraj Ammaiyappan, Christophe Darcel
Summary: By starting from nitroarenes and using hydrosilylation conditions with a well-defined N-heterocyclic carbene iron(0) catalyst, aniline derivatives were successfully produced in moderate to high yields. Furthermore, a selective synthesis of cyclic amines such as pyrrolidines, piperidines, and azepanes was achieved from levulinic acid, 1,5- and 1,6-keto acids, respectively, with isolated yields up to 69% under visible light irradiation and thermal conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Hua Zhao, Peng Shen, Dongru Sun, Hongbin Zhai, Yufen Zhao
Summary: The regioselective functionalization reaction of unprotected carbazoles with donor-acceptor (D-A) cyclopropanes has been successfully demonstrated in this study. By utilizing Lewis acid and Bronsted acid catalysts, N-H and C-H functionalization reactions were carried out selectively, which opens up new possibilities for the synthesis of carbazole-containing heterocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jeremy Marchais, Didier Begue, Alain Dargelos, Curt Wentrup
Summary: The denitrogenative rearrangements of various benzotriazoles were studied using DFT and CASPT2 calculations, showing different reaction pathways for different types of benzotriazoles during pyrolysis or photolysis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Subhendu Pramanik, Sarat Chatterjee, Rumjhum Banerjee, Chinmay Chowdhury
Summary: This study presents a direct synthesis method for carbazoles containing aryl and aryl ketone groups. The reaction involves Pd(II)-catalyzed cascade reactions, which enables the fast assembly of carbazoles through four carbon-carbon bond formations. The absence of aldehyde substrates leads to the formation of C4-aryl-substituted carbazoles. The method is versatile for the synthesis of biscarbazole derivatives.
Article
Chemistry, Organic
Anton A. Merkushev, Anton S. Makarov, Pavel M. Shpuntov, Vladimir T. Abaev, Igor V. Trushkov, Maxim G. Uchuskin
Summary: 2-(2-Acylvinyl)indoles obtained by oxidative rearrangement of substituted 2-(2-aminobenzyl)furans can be used to construct structural analogues of antifungal alkaloids caulindoles A-D and other indole-derived molecules and substituted carbazoles by introducing new reaction centers or manipulating functional groups of the obtained compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Abdul Wahab, Ziwei Gao, Jing Gou, Binxun Yu
Summary: Triazole phosphonates are important structural motifs in chemical biology and have gained increasing interest in recent years. A novel method to synthesize triazolyl phosphonates starting from furfuryl phosphonate alcohols and organo-azides using an intermolecular copper-catalyzed cascade reaction was developed. A three-component reaction strategy was realized for rapid access to triazole phosphonates.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Nikki J. Bakas, Jeffrey D. Sears, William W. Brennessel, Michael L. Neidig
Summary: This study provides critical insights into the role of TMEDA as an additive in iron-catalyzed cross-coupling reactions. By using spectroscopic and crystallographic techniques, TMEDA-iron(II)-aryl intermediates are identified in the reaction cycle and it is found that their recombination with radicals leads to highly selective product formation. This research highlights the significance of TMEDA in modulating the selectivity and catalytic performance of organoiron species in cross-coupling reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Sofya S. Kuvshinova, Yulia Nelyubina, Vladimir A. Larionov, Daria V. Vorobyeva, Sergey N. Osipov, Dmitry A. Loginov
Summary: Novel Rh and Ir complexes were synthesized and their structures were determined by X-ray diffraction. The compounds prepared, as well as related derivatives, efficiently catalyze the alkylation of N-(pyrimidin-2-yl)indole with methyl 3,3,3-trifluoro-2-diazopropionate.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
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)