Peng Xu's research while affiliated with Max Planck Institute for Coal Research and other places

Publications (6)

Article
Full-text available
Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35°C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage ap...
Article
Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35°C via photoinduced ligand‐to‐metal charge transfer (LMCT)‐enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late‐stage ap...
Article
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 mainly by transition-metal-catalyzed decarboxylative cross couplings. However, the high activation barrier for thermal decarboxylative carbometalation th...
Article
Full-text available
Site‐selective functionalization of C−H bonds in small complex molecules is a long‐standing challenge in organic chemistry. Herein, we report a broadly applicable and site‐selective aromatic C−H dibenzothiophenylation reaction. The conceptual advantage of this transformation is further demonstrated through the two‐step C−H [18F]fluorination of a se...
Article
Full-text available
Zur richtigen Zeit am richtigen Ort: Eine breit anwendbare und regioselektive aromatische [¹⁸F]Fluorierung im späten Synthesestadium wurde entwickelt. Ein Satz von drei elektronisch verschiedenen Dibenzothiophenen ermöglicht die ¹⁸F‐Markierung einer Serie niedermolekularer, komplexer Verbindungen. Abstract Site‐selective functionalization of C−H b...
Article
Methods for direct benzonitrile synthesis are sparse, despite the versatility of cyano groups in organic synthesis and the importance of benzonitriles for the dye, agrochemical, and pharmaceutical industries. We report the first general late-stage aryl C–H cyanation with broad substrate scope and functional-group tolerance. The reaction is enabled...

Citations

... 28b Very recently, anhydrous TBAF(tBuOH) 4 was successfully employed as a fluorinating reagent in the radical fluorodecarboxylation of benzoic acids in acetonitrile; its use suppressed competing C−O reductive elimination observed when using TBAF. 29 An early synergistic approach to fluorination with KF was reported by Lee, Chi, Song, and co-workers. 30 Achiral polyethers with a pending alcohol (e.g., tri-or tetraethylene glycol) were employed as solvents in order to encapsulate the cation of an inorganic fluoride salt while simultaneously modulating the reactivity of fluoride and activating the electrophile through hydrogen bonding. ...
... Beside the diaryliodonium salts, aryldibenzothiophenium salts can be used as another catalyzer for synthesizing non-activated arene [ 18 (Fowler et al., 2015), were successfully radiosynthesized by this [ 18 (Xu et al., 2020). Significantly, they showed how electronically different dibenzothiophenes appropriately matched the electronic requirements of the arene. ...
... Thus, strategies such as transition-metal catalysis, [26][27][28][29] hypervalent iodine reagents, [30][31][32] and phase-transfer catalysis [33][34][35] have been employed widely to achieve fluorination with Selectfluor or NFSI (Figure 1b). Recently, Ritter and co-workers [36][37][38][39] and Sanford's group [40][41][42][43] generated elegantly, transition-metal-catalyzed fluorinated arenes with unreactive N-F reagents. Liu [44][45][46][47][48][49] and Zhang,50 independently, obtained the significant fluoroamination of styrenes with NFSI via fluoropalladation and copper-catalyzed radical strategy. ...
... 37 Based on our own interest in the redox chemistry in similar reactions catalyzed by palladium carboxylates, specifically dinuclear Pd(III) chemistry, 38 and the concepts developed by others in this area, most prominently by Sanford 39 and Yu, 37 we contributed a C−H cyanation (Scheme 10, eq 2). 40 A remaining challenge in this chemistry deals with the modularity of the coupling partner, e.g., nucleophiles other than cyanide, not all of which can currently be added with the same efficiency. The in situ-generated Ar−[Pd] organometallic intermediate should, in principle, be useful as a broadly diversifiable linchpin, to be converted into a wide variety of substituents; however, the ligands and reaction conditions employed for efficient C−H metalation must also meet the requirements for efficient C−X bond formation, which is often not yet the case. ...