Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes

Rottschäfer, Dennis; Neumann, Beate; Stammler, Hans-Georg; van Gastel, Maurice; Andrada, Diego M.; Ghadwal, Rajendra S.

doi:10.1002/anie.201801596

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes

MPS-Authors

/persons/resource/persons216842

van Gastel, Maurice
Research Group van Gastel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

Rottschäfer, D., Neumann, B., Stammler, H.-G., van Gastel, M., Andrada, D. M., & Ghadwal, R. S. (2018). Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes. Angewandte Chemie International Edition, 57(17), 4765-4768. doi:10.1002/anie.201801596.

Cite as: https://hdl.handle.net/21.11116/0000-0001-706F-5

Abstract

One‐electron reduction of C2‐arylated 1,3‐imidazoli(ni)um salts (IPr^Ar)Br (Ar=Ph, 3 a; 4‐DMP, 3 b; 4‐DMP=4‐Me₂NC₆H₄) and (SIPr^Ar)I (Ar=Ph, 4 a; 4‐Tol, 4 b) derived from classical NHCs (IPr=:C{N(2,6‐iPr₂C₆H₃)}₂CHCH, 1; SIPr=:C{N(2,6‐iPr₂C₆H₃)}₂CH₂CH₂, 2) gave radicals [(IPr^Ar)]. (Ar=Ph, 5 a; 4‐DMP, 5 b) and [(SIPr^Ar)]. (Ar=Ph, 6 a; 4‐Tol, 6 b). Each of 5 a,b and 6 a,b exhibited a doublet EPR signal, a characteristic of monoradical species. The first solid‐state characterization of NHC‐derived carbon‐centered radicals 6 a,b by single‐crystal X‐ray diffraction is reported. DFT calculations indicate that the unpaired electron is mainly located at the original carbene carbon atom and stabilized by partial delocalization over the adjacent aryl group.