Edgar Haak

Edgar Haak
Otto-von-Guericke-Universität Magdeburg | OvGU · Chemical Institute (ICH)

Dr.

About

39
Publications
1,487
Reads
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627
Citations
Additional affiliations
April 2008 - present
Otto-von-Guericke-Universität Magdeburg
Position
  • Jun.-Professor
November 2003 - March 2008
Technische Universität Braunschweig
Position
  • Habilitand
March 2002 - June 2003
Université de Montréal
Position
  • PostDoc Position

Publications

Publications (39)
Article
Full-text available
Various triaminocyclopentadienyl ruthenium complexes have been synthesized from Ru3(CO)12. The new complexes were tested for their ability to catalyze cascade conversions of propargyl alcohols. Their associated catalytic activities complement the activities of known diaminocyclopentadienone ruthenium complexes. In particular, the substrate scope of...
Article
Full-text available
Electroenzymatic processes are interesting solutions for the development of new processes based on renewable feedstocks, renewable energies, and green catalysts. High-selectivity and sustainability of these processes are usually assumed. In this contribution, these two aspects were studied in more detail. In a membrane-less electroenzymatic reactor...
Article
2,3-Annulated indoles exhibit a broad spectrum of biological activities. Various annulation strategies are applied to generate these scaffolds from prefunctionalized aniline or indole derivatives. Only a few methodologies allow the direct annulation of indole itself, often associated with regioselectivity issues or restrictions on available substit...
Article
Multiple bond-forming cascade transformations and one-pot procedures provide rapid access to natural product-like scaffolds from simple precursors. These atom-economical processes are valuable tools in organic synthesis and drug discovery. Herein, we report on ruthenium-catalyzed cascade annulations of indole with readily available propargyl alcoho...
Article
Multiple bond-forming cascade transformations and one-pot procedures provide rapid access to natural product-like scaffolds from simple precursors. These atom-economical processes are valuable tools in organic synthesis and drug discovery. Herein, we report on ruthenium-catalyzed cascade annulations of indole with readily available propargyl alcoho...
Article
Multiple bond-forming cascade transformations and one-pot procedures are valuable tools in organic synthesis and drug discovery. These atom-economical processes provide rapid access to natural product-like scaffolds from simple precursors. Herein, we report on ruthenium-catalyzed one-pot conversions of simple 1-alkenyl propargyl alcohols with cycli...
Article
A short and efficient total synthesis of the cytotoxic cyclopent[g]indole alkaloid (±)-herbindole A from dihydromesitylene has been achieved by incorporating a ruthenium-catalyzed allylation–cycloisomerization cascade reaction as the key step. The protocol has also been applied to the synthesis of the unnatural trans-epimer of the marine natural pr...
Article
It is the aim of this microreview to highlight the diversity of structural conversions that are accessible from 1-alkenylpropargyl alcohols and esters in the context of transition-metal-catalyzed cascade transformations. These readily available enynols facilitate diverse transition-metal-catalyzed cascade reactions, exploiting their different funct...
Article
Full-text available
Lightweight design is an essential part of the overall Volkswagen strategy for reducing the CO2 emissions. The use of carbon fiber offers an enormous lightweight potential. In comparison to steel enabling a mass reduction of up to 70% in automotive parts without a degradation of the functionalities is possible. Today, the use of carbon fiber is lim...
Article
Ruthenium-catalyzed cascade transformations for the synthesis of 2,3-cyclo[3]dendralenes and multicomponent processes based thereon to generate complex polycycles are presented. The combination of allylation-cyclization sequences with diene-transmissive Diels-Alder reactions allows the rapid and selective construction of natural-product-like motifs...
Article
Rutheniumkatalysierte Kaskadentransformationen zur Synthese von 2,3-Cyclo[3]dendralenen und darauf basierende Mehrkomponentenprozesse zum Aufbau komplexer Polycyclen werden vorgestellt. Die Kombination von Allylierungs-Cyclisierungs-Sequenzen mit Dien-transmissiven Diels-Alder-Reaktionen ermöglicht den schnellen und selektiven Aufbau naturstoffähnl...
Article
Ruthenium-catalyzed atom-economic transformations of 1-vinylpropargyl alcohols with amines leading to highly substituted pyrroles in a one-pot cascade process are reported. The allylation/cycloisomerization sequence is catalyzed by a single ruthenium(0) complex that contains a redox-coupled dienone ligand and can be extended by an additional [3,3]...
Article
Ruthenium-catalyzed allylation-cyclization reactions of cyclic 1,3-dicarbonyl compounds with 1-vinyl propargyl alcohols that lead to diverse carbo- or heterocyclic products in a one-pot cascade process are reported. These mechanistically distinct reactions are catalyzed by a single ruthenium(0) complex that contains a redox-coupled dienone ligand....
Article
Several ruthenium-catalyzed atom-economic transformations of propargyl alcohols with pyrroles or indoles leading to alkylated, propargylated, or annulated heteroaromatics are reported. The mechanistically distinct reactions are catalyzed by a single ruthenium(0) complex containing a redox-coupled dienone ligand. The mode of activation regarding the...
Article
Monomeric ruthenium(0) complexes containing redox-coupled dienone ligands were found to catalyze the regio-selective addition of carboxylic acids or cyclic 1,3-dicarbonyl compounds to propargyl alcohols.
Article
Aliphatic azidonitriles separated by three or four carbon atoms undergo facile Lewis acid-induced cycloadditions to give bicyclic tetrazoles, even at 0 degrees C. Extension to 3-azido-2-aryl-1,3-dioxolanes and the corresponding 1,3-dioxanes in the presence of TMSCN and BF3.OEt2 leads to a series of diversely functionalized novel oxabicyclic tetrazo...
Article
Ruthenium complexes of redox-coupled cyclopentadienone ligands catalyze the formation of allenyl carbamates from propargyl alcohols and isocyanates. This efficient and atom-economical process represents the first catalytic access to allenyl carbamates, compounds of high synthetic potential. The reaction needs an acidic co-catalyst and can be perfor...
Article
A series of donor- and acceptor-substituted ruthenium cyclopentadienone complexes were synthesized and their catalytic activities towards propargyl alcohols focused on amination reactions have been investigated. It is shown that the substituents of the cyclopentadienone ligand determine the mode of activation of propargyl alcohols by these complexe...
Article
Monomeric ruthenium(0) complexes containing electronically coupled dienone ligands were found to catalyze the fort-nation of enammoketones from propargyl alcohols.
Article
The condensation of enaminoketone 8 to alpha-hydroxyketones gives rise to nonsymmetric pyrazines. This may be of relevance for the biosynthesis of this heterocycle in the cephalostatins and ritterazines.
Article
A new and highly flexible procedure for the synthesis of α,α-disubstituted α-amino phosphonates is described with disubstituted alkynes, primary amines and diethyl or dimethyl phosphite as starting materials. The reaction sequence, which is performed as a one-pot operation, starts with a Cp2TiMe2-catalyzed hydroamination of the alkyne. A subsequent...
Article
A new and highly flexible procedure for the synthesis of alpha,alpha-disubstituted alpha-amino phosphonates is described with disubstituted alkynes, primary amines and diethyl or dimethyl phosphite as starting materials. The reaction sequence, which is performed as a one-pot operation, starts with a Cp2TiMe2-catalyzed hydroamination of the alkyne....
Article
Commercially available alpha-aminodiphenylmethane 1 (benzhydrylamine) serves as a convenient ammonia equivalent in the dimethyltitanocene-catalyzed intermolecular hydroamination of alkynes. The primary formed imines can be hydrogenated and cleaved directly to the corresponding primary amines by catalytic hydrogenation using Pd/C as catalyst.
Article
A completely new application of dimethyltitanocene as catalyst for the intermolecular hydroamination of alkynes is presented. With this inexpensive and readily available catalyst, alkynes can be easily converted into imines, amines, and ketones (see reaction scheme).
Article
Eine völlig neue Verwendung findet Dimethyltitanocen als Katalysator in der intermolekularen Hydroaminierung von Alkinen. Mit diesem preisgünstigen und problemlos handhabbaren Katalysator können Alkine einfach in Imine, Amine und Ketone überführt werden (siehe Schema).
Article
Bei der Hydroaminierung von Alkenen und Alkinen handelt es sich um Reaktionen, die auch 1999 noch nicht zum Standardwerkzeug der Organischen Chemie gehören. Viele der hier beschriebenen Verfahren sind auf einzelne Substratklassen oder sogar einzelne Substrate beschränkt, verwenden hochempfindliche und teure Katalysatoren (z. R. Lanthanoidverbindung...
Article
Nitrogen containing molecules are among the most important classes of chemical substances. They play an outstanding role as biologically active compounds as well as industrial chemicals. In the past these facts lead to the development of a large number of methods for the synthesis of amines, imines and enamines. While most of these well established...
Chapter
Präoperative Gerinnungsuntersuchungen sollen insbesondere bei elektiven Eingriffen die Diagnose erworbener oder angeborener Blutungsneigungen ermöglichen. Im allgemeinen werden Suchtests der plasmatischen Gerinnung (Prothrombinzeit und partielle Thromboplastinzeit) sowie die Zählung der Thrombozyten gefordert. Mancherorts ist die Bestimmung der Blu...

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