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.

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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://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.

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