Publication
Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C-H Functionalizations
Publications associées (43)
Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling
Paul Joseph Dyson, Mingyang Liu
Efficient valorization of lignin, a sustainable source of functionalized aromatic products, would reduce dependence on fossil-derived feedstocks. Oxidative depolymerization is frequently applied to lignin to generate phenolic mono- mers. However, due to th ...
2023Palladium-Catalyzed trans-Hydroalkoxylation: Counterintuitive Use of an Aryl Iodide Additive to Promote C-H Bond Formation
Jérôme Waser, Mikus Purins, Ashis Kumar Das, Luca Buzzetti
We report an enantioselective palladium-catalyzed trans-hydroalkoxylation of propargylic amines with a trifluoroacetaldehydederived tether to build chiral oxazolidines. Diastereoselective hydrogenation using a heterogeneous palladium catalyst then gave acc ...
AMER CHEMICAL SOC2022Catalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoamides Catalyzed by a Single H‐Bond Donor Organocatalyst
Jieping Zhu, Qiang Wang, Rémi Julien Sylvain Andres
The asymmetric Pictet–Spengler reaction (PSR) with aldehydes is well known. However, PSR involving ketones as electrophilic partners is far-less developed. We report herein the first examples of catalytic enantioselective PSR of tryptamines with α-ketoamid ...
2022Catalytic Enantioselective Synthesis of Morpholinones Enabled by Aza-Benzilic Ester Rearrangement
Qian Wang, Jieping Zhu, Hua Wu, Yuping He
Chiral morpholinone is an important building block in organic synthesis and a pharmacophore in medicinal chemistry. However, catalytic enantioselective methods for the construction of this N,O-heterocycle remain scarce. We report herein a chiral phosphoric ...
2021Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation
Phillip Gulliver Dominic Greenwood
a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that
can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons,
they constitute privileged targets for the development of ne ...
EPFL2020Mechanistic Studies of Two Ni-Catalyzed Reactions: Reductive Amidation of Esters with Nitroarenes and Hydrosilylation of Alkenes
Mechanistic investigations into homogeneously catalyzed reactions are essential for the fur-ther development of synthetic methodologies. Insights in the overall reaction pathway and vital steps such as the rate-determining and selectivity-determining steps ...
EPFL2020Biomimetic Hydrogenation Catalyzed by a Manganese Model of [Fe]-Hydrogenase
[Fe]‐hydrogenase is an efficient biological hydrogenation catalyst. Despite intense research, Fe complexes mimicking the active site of [Fe]‐hydrogenase have not achieved turnovers in hydrogenation reactions. Herein, we describe the design and development ...
2020Synthetic methodologies for C-C and C-N bond formation involving alkyl radicals
C-C and C-N bonds are some of the most common structures in molecules ranging from drugs to catalysts and to food additives. Many coupling reactions were developed to form these types of bonds with excellent selectivity and good performance. Still, the syn ...
EPFL2020Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C-H Functionalizations
Nicolai Cramer, Daria Grosheva
Asymmetric metal-catalyzed C-H functionalization is a powerful strategy for the rapid generation of complex target molecules from simple precursors. While aryl (pseudo) halides have been used as electrophilic substrates in enantioselective Pd(0)-catalyzed ...
SWISS CHEMICAL SOC2019Pd Nanoparticles Stabilized by Hypercrosslinked Polystyrene Catalyze Selective Triple C-C Bond Hydrogenation and Suzuki Cross-Coupling
This paper describes the synthesis of Pd-containing catalysts based on nonfunctionalized hypercrosslinked polystyrene via impregnation with Pd acetate. Developed Pd nanoparticulate catalyst allowed achieving conversion of aryl halide up to 90% in Suzuki cr ...
2019