ORCID Profile
0000-0003-0247-4384
Current Organisation
RWTH Aachen University
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Organic chemical synthesis | Catalysis and mechanisms of reactions | Organic Chemistry | Organic chemistry | Organic Chemical Synthesis
Publisher: Wiley
Date: 04-02-2019
Publisher: American Chemical Society (ACS)
Date: 18-06-2020
Publisher: American Chemical Society (ACS)
Date: 07-08-2020
Publisher: Wiley
Date: 04-02-2019
Abstract: The functionalization of C-H bonds with non-precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron porphyrin catalyzed reactions of diazoacetonitrile with N-heterocycles yielding important precursors of tryptamines, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C-H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.
Publisher: Wiley
Date: 10-02-2022
Abstract: Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen‐bonding networks, in order to enhance its catalytic activity to achieve a desired reaction outcome, is less explored in organic synthesis, despite being a commonly found phenomenon in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl‐olefin metathesis reactions by hydrogen‐bonding‐assisted Brønsted acid catalysis, using hexafluoroisopropanol (HFIP) solvent in combination with para ‐toluenesulfonic acid (pTSA). Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting pTSA Brønsted acid catalyst, but also insightful knowledge about the current limitations of the carbonyl‐olefin metathesis reaction.
Publisher: American Chemical Society (ACS)
Date: 16-10-2019
DOI: 10.1021/ACS.ORGLETT.9B03453
Abstract: Cyclopropanation reactions of carbenes with arenes provide a straightforward pathway to norcaradienes or cycloheptatrienes. This reaction normally requires harsh reaction conditions or transition-metal catalysts. In this report, we describe the metal-free visible-light photolysis of aryl diazoacetates in aromatic solvents, which provides access to the norcaradiene ring system in a highly regio- and stereoselective manner. The mild reaction conditions of this approach also allow chemoselective cyclopropanation of substituted arenes without competing C-H functionalization reactions.
Publisher: Wiley
Date: 10-02-2022
Abstract: Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen‐bonding networks, in order to enhance its catalytic activity to achieve a desired reaction outcome, is less explored in organic synthesis, despite being a commonly found phenomenon in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl‐olefin metathesis reactions by hydrogen‐bonding‐assisted Brønsted acid catalysis, using hexafluoroisopropanol (HFIP) solvent in combination with para ‐toluenesulfonic acid (pTSA). Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting pTSA Brønsted acid catalyst, but also insightful knowledge about the current limitations of the carbonyl‐olefin metathesis reaction.
Publisher: American Chemical Society (ACS)
Date: 05-01-2021
Publisher: American Chemical Society (ACS)
Date: 31-08-2020
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7CC02033C
Abstract: The Wittig-type chemical procedure is adapted to efficiently facilitate alkyl–alkyl coupling reactions in batch and flow.
Publisher: American Chemical Society (ACS)
Date: 07-2021
DOI: 10.26434/CHEMRXIV-2021-GPLLR
Abstract: Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen bonding networks, in order to control its catalytic activity to achieve desired reaction outcomes is much less explored in organic synthesis, despite being a common strategy in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl-olefin metathesis reactions by hydrogen bonding-assisted Brønsted acid catalysis. The carbonyl-olefin metathesis reaction has recently emerged as a powerful synthetic tool for functional group interconversion of carbonyls and alkenes. However, the application of Brønsted acid catalysts in carbonyl-olefin metathesis reaction, especially in homogeneous conditions, remains scarce and poorly understood. In this work, we report the use of hexafluoroisopropanol solvent in combination with para-toluenesulfonic acid to efficiently catalyze carbonyl-olefin metathesis reactions. Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting this Brønsted acid catalyzed reaction but also insightful knowledge about the current limitations of the carbonyl-olefin metathesis reaction.
Publisher: American Chemical Society (ACS)
Date: 17-07-2017
Abstract: Trifluoromethyl-substituted cyclopropanes are an attractive family of building blocks for the construction of pharmaceutical and agrochemical agents. This work demonstrated the utilization of fluorinated sulfur ylides as versatile reagents for Corey-Chaykovsky cyclopropanation reactions of nitro styrenes. This protocol favored the synthesis of cis-configured trifluoromethyl cyclopropanes for a broad range of substrates with excellent yields and good diastereoselectivities.
Publisher: Wiley
Date: 12-11-2020
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8CC07329E
Abstract: We report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro -Claisen-type reactions.
Publisher: American Chemical Society (ACS)
Date: 15-10-2020
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8CC05602A
Abstract: A readily available sulfonium salt opens up new synthetic pathways to access nitrile cyclopropanes in a highly diastereoselective fashion.
Publisher: Wiley
Date: 25-02-2020
Publisher: Wiley
Date: 20-01-2020
Publisher: Wiley
Date: 12-01-2021
Abstract: Herein we describe a multiple C−H functionalization reaction of carbazole heterocycles with diazoalkanes. We show that gold catalysts play a distinct role in enabling a multiple C−H functionalization reaction to introduce up to six carbene fragments onto molecules containing multiple carbazole units or to link multiple carbazole units into a single molecule. A one‐pot stepwise approach enables the introduction of two different carbene fragments to allow orthogonal deprotection and straightforward derivatization.
Publisher: American Chemical Society (ACS)
Date: 20-08-2020
DOI: 10.26434/CHEMRXIV.12824921.V1
Abstract: Acyl transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl transfer reaction. Herein we introduce a new acyl transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give the products with excellent efficiency under thermal or blue light-photochemical conditions. Kinetic studies and density functional theory (DFT) calculations suggest interesting mechanistic insights for reactions promoted by this new acyl transfer catalytic system.
Start Date: 07-2023
End Date: 07-2023
Amount: $1,083,292.00
Funder: Australian Research Council
View Funded ActivityStart Date: 2020
End Date: 12-2023
Amount: $420,000.00
Funder: Australian Research Council
View Funded Activity