Stable Carbon-Centered Radicals Based on N-Heterocyclic Carbenes

Ghadwal R (2019)
Synlett 30(15): 1765-1775.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Carbon-centered radicals and diradicaloids based on classical N-heterocyclic carbene (NHC) scaffolds are readily accessible as crystalline solids. The presence of an aryl (Ar) substituent at the C2-position is the key to the remarkable stability of these open-shell species as it provides appropriate room for the spin-density delocalization. Two catalytic as well as high-yielding protocols have been developed to install a suitable aryl group at the C2-position of NHCs. The spin-density in mono-radicals (NHCAr)(center dot) is mostly located on the parent carbene carbon (C2) atom. The bridging of two NHCs through a phenylene spacer (C6H4)(n) enables the isolation of various p-quinodimethane (p-QDM) derivatives, which may be considered as open-shell Kekule diradicaloids. The diradical character of these NHC-analogues of Thiele (n = 1), Chichibabin (n = 2), and Muller (n = 3) hydrocarbons [(NHC)(C6H4)(n)(NHC)] can be tuned by a rational choice of the size and/or the topology of spacers. In this account, the synthesis, structure, and properties of this new class of radical hydrocarbons is presented.
Stichworte
radical; diradical; diradicaloid; carbene; hydrocarbon; heterocycle; open-shell; paramagnetic
Erscheinungsjahr
2019
Zeitschriftentitel
Synlett
Band
30
Ausgabe
15
Seite(n)
1765-1775
ISSN
0936-5214
eISSN
1437-2096
Page URI
https://pub.uni-bielefeld.de/record/2937332

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Ghadwal R. Stable Carbon-Centered Radicals Based on N-Heterocyclic Carbenes. Synlett. 2019;30(15):1765-1775.
Ghadwal, R. (2019). Stable Carbon-Centered Radicals Based on N-Heterocyclic Carbenes. Synlett, 30(15), 1765-1775. doi:10.1055/s-0037-1611887
Ghadwal, R. (2019). Stable Carbon-Centered Radicals Based on N-Heterocyclic Carbenes. Synlett 30, 1765-1775.
Ghadwal, R., 2019. Stable Carbon-Centered Radicals Based on N-Heterocyclic Carbenes. Synlett, 30(15), p 1765-1775.
R. Ghadwal, “Stable Carbon-Centered Radicals Based on N-Heterocyclic Carbenes”, Synlett, vol. 30, 2019, pp. 1765-1775.
Ghadwal, R.: Stable Carbon-Centered Radicals Based on N-Heterocyclic Carbenes. Synlett. 30, 1765-1775 (2019).
Ghadwal, Rajendra. “Stable Carbon-Centered Radicals Based on N-Heterocyclic Carbenes”. Synlett 30.15 (2019): 1765-1775.