Aryldiazonium salts remain a staple in organic synthesis and are still prepared largely in accord with the protocol developed in the 19th century. Because of the favorable reactivity that often...

Nature Chemistry - Cysteine bioconjugation is an important method to modify biomolecules, but synthetic efforts to diversify reactive warheads and the low reactivity of introducible linchpins often...

Herein, we report the first bench-stable and nonhygroscopic monosubstituted allenyl sulfonium salt (ATT) synthesized from thianthrene and propargyl alcohol. We demonstrate its use in annulation...

Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF3+OTf–) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from...

Direct C–H fluorination is an efficient strategy to construct aromatic C–F bonds, but the cleavage of specific C–H bonds in the presence of other functional groups and the high barrier of C–F bond...

Abundant aromatic carboxylic acids exist in great structural diversity from nature and synthesis. To date, the synthetically valuable decarboxylative functionalization of benzoic acids is realized...

The use of vinyl electrophiles in synthesis has been hampered by the lack of access to a suitable reagent that is practical and of appropriate reactivity. In this work we introduce a vinyl thianthr...

Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF3+OTf–) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from...

The arylethylamine pharmacophore is conserved across a range of biologically active natural products and pharmaceuticals, particularly in molecules that act on the central nervous system. Herein, we...

Nature Catalysis - Hydrofunctionalization of α-olefins with mineral acids usually proceeds with Markovnikov selectivity. Now, a strategy based on synergistic phase transfer and photoredox...

Nature - A highly site-selective aromatic C–H functionalization reaction that does not require a particular directing group or arene substitution pattern provides functionalized arenes that...

Herein, we report a photoinduced sulfoximine-to-copper charge-transfer-enabled generation of sulfoximinyl radicals directly from NH-sulfoximines for C–H sulfoximination of arenes via radical additi...

Nature Catalysis - Photoredox-catalysed coupling of electron-rich aryl electrophiles based on simple nickel salts usually suffers from a slow oxidative addition. Now, it is shown that...

Utilizing readily available and cost-effective aryl halides, amines, and butadienes as starting materials, in conjunction with rac-BINAP and a Pd catalyst, we can efficiently synthesize highly...

Here we report an unprecedented reductive vinylation of alkyl iodides, which expands on the currently possible reductive Csp2-Csp3 cross-coupling reactions.

Catalytic π-arene activation is based on catalysts that allow for arene exchange. To date, cyclopentadiene (Cp)-derived catalysts are the most commonly used in π-arene activation despite their low...

Herein, a regioselective, late-stage two-step arene halogenation method is reported. We propose how unusual Ni(I)/(III) catalysis is enabled by a combination of aryl thianthrenium and Ni redox...

Late-stage functionalization of C–H bonds (C–H LSF) can provide a straightforward approach to the efficient synthesis of functionalized complex molecules. However, C–H LSF is challenging because the...

We report α-thianthrenium carbonyl species as α-carbonyl carbocation equivalents, generated in situ by radical conjugate addition of trifluoromethyl radical to Michael acceptors. The method can...

Herein, we present an undirected para-selective two-step C–H alkylation of complex arenes useful for late-stage functionalization. The combination of a site-selective C–H thianthrenation with...

We show the conversion of unactivated alkenes into α-branched α,β-unsaturated ketones (enones) and esters. Regioselective chloroacylation with acyl chlorides and chloroformates takes place under...

Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C–H iodination of (hetero)arenes with a broad functional group...

The introduction of thianthrene as a linchpin has proven to be a versatile strategy for the C–H functionalization of aromatic compounds, featuring a broad scope and fast diversification. The synthe...

Synthetic methods for oxidative aromatic C–O bond formation are sparse, despite their demand in metabolite synthesis for drug discovery and development. We report a novel methodology for late-stage...

Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF3+OTf–) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from...

We report diverse C–N cross-coupling reactions of aryl thianthrenium salts that are formed site-selectively by direct C–H functionalization. The scope of N-nucleophiles ranges from primary and...

The author discusses a safety hazard that occurred in his laboratory.

18F-fluorination is an important and growing field in organic synthesis that has attracted many chemists in the recent past. Here we present our own, biased perspective with a focus on our own...

Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to...

On this week’s show: Researchers try to identify effective loneliness interventions, making the Sandmeyer reaction safer, and books that look to the future and don’t see doom and gloom

A new mode of activation of sulfonium salts by α-amino alkyl radicals is reported. The C−S bond of the aryl sulfonium salt is cleaved by the action of α-amino alkyl radicals in the absence of light...

Researchers of the Department of Organic Synthesis at the Max-Planck-Institut für Kohlenforschung developed a C-H functionalization reaction that proceeds wi...

Zur Klärung der Ursachen einer schweren Explosion bei der Diazotierung von 6-Chlor-2,4-dinitro-anilin wurde die thermische Stabilität verschiedener Diazotierungs-massen mit Hilfe mechanischer,...

Aryl sulfinates are precursors to a diverse number of sulfonyl-derived arenes, which are common motifs in pharmaceuticals and agrochemicals. Here, we report a site-selective two-step C–H sulfination...

Unsere Gruppe entwickelt organische und metallorganische Reaktionschemie, die für die Katalyse, Medizin und Materialien relevant ist.