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Ferrocene‐Based N‐Heterocyclic Carbenes with Functionalised Benzyl Substituents
Author(s) -
Thie Charlotte,
Bruhn Clemens,
Siemeling Ulrich
Publication year - 2015
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201500977
Subject(s) - chemistry , deprotonation , ring (chemistry) , ferrocene , electrophile , medicinal chemistry , heteroatom , carbene , organic chemistry , catalysis , ion , electrochemistry , electrode
We describe herein N‐heterocyclic carbenes (NHCs) with a 1,1′‐ferrocenylene backbone that contain substituents at the nitrogen atoms relevant for applications in the area of metallopharmaceuticals, namely benzyl units functionalised with dimethylamino and methoxy groups at the para position. These carbenes are too unstable for isolation. They were generated from the corresponding formamidinium tetrafluoroborates by deprotonation and efficiently trapped in situ. Trapping with elemental selenium afforded the corresponding selenourea derivatives, the 77 Se NMR chemical shifts of which are in accord with the comparatively high electrophilicity typical of expanded‐ring NHCs. Coordinative trapping with [{Rh(μ‐Cl)(cod)} 2 ] (cod = cycloocta‐1,5‐diene) furnished air‐stable complexes of the type [RhCl(cod)(NHC)], the benzyl CH 2 groups of which are engaged in pronounced anagostic C–H···Rh interactions, both in solution and in the solid state.