Bis(pyrazol-1-yl)acetic acid bearing ferrocenyl substituents
Tampier S, Bleifuß S, Abd-Elzaher MM, Sutter J, Heinemann FW, Burzlaff N (2013)
Publication Type: Journal article, Original article
Publication year: 2013
Journal
Original Authors: Tampier S., Bleifuss S.M., Abd-Elzaher M.M., Sutter J., Heinemann F.W., Burzlaff N.
Publisher: American Chemical Society
Book Volume: 32
Pages Range: 5935-5945
Journal Issue: 20
DOI: 10.1021/om400495f
Abstract
The new compound 4-ferrocenyl-3,5-dimethylpyrazole (4; fcdmpzH) has been synthesized from 4-iodo-3,5-dimethyl-1-tritylpyrazole (2) via a Negishi type cross-coupling reaction and subsequent deprotection of the intermediate 4-ferrocenyl-3,5-dimethyl-1-tritylpyrazole (3; fcdmpzTrt). Reaction of the pyrazole 4 with dichloromethane, base, and phase transfer catalyst results in the chelating N,N ligand bis(4-ferrocenyl-3,5-dimethylpyrazol-1-yl)methane (5; bfcdmpzm). Bis(4-ferrocenyl-3,5-dimethylpyrazol-1-yl)ketone (6; bfcdmpzk) is obtained by reacting 4 with NEt and triphosgene. The N,N,O heteroscorpionate ligand bis(4-ferrocenyl-3,5-dimethylpyrazol-1-yl)acetic acid (7; H[bfcdmpza]) can be accessed by reacting pyrazole 4 with dibromoacetic acid, KOtBu, and phase transfer catalyst and subsequent acidic workup. The heteroscorpionate ligand H[bfcdmpza] (7) is suitable to bind metal ions in a κ coordination mode, as could be proven by the formation of a the bis-ligand complex [Fe(bfcdmpza)] (8). The molecular structures of 3, 5, 6, and 8 have been obtained by single-crystal X-ray structure determination. The electrochemical properties of the four ferrocenyl-substituted compounds 3-6 have been studied by cyclic voltammetric measurements and discussed as well. © 2013 American Chemical Society.
Authors with CRIS profile
Sascha Bleifuß
Professur für Anorganische Chemie
Jörg Sutter
Lehrstuhl für Anorganische und Allgemeine Chemie
Frank Wilhelm Heinemann
Lehrstuhl für Anorganische und Allgemeine Chemie
Nicolai Burzlaff
Professur für Anorganische Chemie
Involved external institutions
Egypt (EG)How to cite
APA:
Tampier, S., Bleifuß, S., Abd-Elzaher, M.M., Sutter, J., Heinemann, F.W., & Burzlaff, N. (2013). Bis(pyrazol-1-yl)acetic acid bearing ferrocenyl substituents. Organometallics, 32(20), 5935-5945. https://dx.doi.org/10.1021/om400495f
MLA:
Tampier, Stefan, et al. "Bis(pyrazol-1-yl)acetic acid bearing ferrocenyl substituents." Organometallics 32.20 (2013): 5935-5945.
BibTeX: Download