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Title: An electrochemically controlled release of NHCs using iron bis(dithiolene) N-heterocyclic carbene complexes
A series of five coordinated iron bis(dithiolene) complexes [Fe(NHC)(S 2 C 2 R 2 ) 2 ] (R = C 6 H 5 or C 6 H 4 - p -OCH 3 ) containing N-heterocyclic carbene (NHC) (NHC = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene or 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene) were isolated in high yield (84–92%). The iron complexes were characterized by NMR spectroscopy and confirmed by single crystal X-ray diffraction studies. The combination of cyclic voltammetry and spectroelectrochemical analysis revealed that iron complexes undergo Fe–C NHC bond cleavage and release NHC upon subjection to electrochemical reduction. The electrochemically released NHC was trapped using 1-naphthylisothiocyanate and the adduct was isolated in nearly quantitative yield (∼99%). As a proof of concept, the electrochemically released NHC was subsequently used as a catalyst for synthesis of γ-butyrolactones from commercially available cinnamaldehydes.  more » « less
Award ID(s):
1904825
PAR ID:
10230511
Author(s) / Creator(s):
; ; ;
Date Published:
Journal Name:
Inorganic Chemistry Frontiers
Volume:
8
Issue:
1
ISSN:
2052-1553
Page Range / eLocation ID:
59 to 71
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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