1508320-23-7Relevant academic research and scientific papers
Bicyclic (Alkyl)(amino)carbenes (BICAACs): Stable Carbenes More Ambiphilic than CAACs
Tomás-Mendivil, Eder,Hansmann, Max M.,Weinstein, Cory M.,Jazzar, Rodolphe,Melaimi, Mohand,Bertrand, Guy
, p. 7753 - 7756 (2017)
A straightforward strategy allows for the synthesis of storable bicyclic (alkyl)(amino)carbenes (BICAACs), which feature enhanced σ-donating and -accepting properties compared to monocyclic (alkyl)(amino)carbenes (CAACs). Due to the bicyclo[2.2.2]octane skeleton, the steric environment around the carbene center is different from that of CAACs and similar to that observed in classical N-heterocyclic carbenes. The different electronic properties of BICAACs as compared to CAACs allow for ligand exchange reactions not only at a metal center, but also at main group elements.
Organic Redox Systems Based on Pyridinium-Carbene Hybrids
Antoni, Patrick W.,Bruckhoff, Tim,Hansmann, Max M.
supporting information, p. 9701 - 9711 (2019/06/17)
New redox systems with three oxidation states are highly sought-after, for example, for redox-flow battery applications, selective reducing agents, or organic electronics. Herein, we describe a straightforward and modular synthesis of a new class of such
Pyrylenes: A New Class of Tunable, Redox-Switchable, Photoexcitable Pyrylium-Carbene Hybrids with Three Stable Redox-States
Antoni, Patrick W.,Hansmann, Max M.
supporting information, p. 14823 - 14835 (2018/11/02)
A new synthetic and modular access to a large family of redox-switchable molecules based upon the combination of pyrylium salts and carbenes is presented. The redox-properties of this new molecule class correlate very well with the π-accepting properties of the corresponding carbenes. While the pyrylium moiety acts as a chromophore, the carbene moiety can tune the redox-properties and stabilize the corresponding radicals. This leads to the isolation of the first monomeric pyranyl-radical in the solid-state. The three stable oxidation states could be cleanly accessed by chemical oxidation, characterized by NMR, EPR, UV-vis, and X-ray diffraction and supported by (TD)-DFT-calculations. The new hybrid class can be utilized as an electrochemically triggered switch and as a powerful photoexcited reductant. Importantly, the pyrylenes can be used as novel photocatalysts for the reductive activation of aryl halides and sulfonamides by consecutive visible light induced electron transfer processes.
