Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

Celine Bittner; Dirk Bockfeld; Matthias Tamm

doi:10.3762/bxiv.2019.71.v1

Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

Celine Bittner,
Dirk Bockfeld and
Matthias Tamm

Submitting author affiliation: Technische Universität Braunschweig, Braunschweig, Germany

Beilstein Arch. 2019, 201971. doi:10.3762/bxiv.2019.71.v1

Published 16 Jul 2019

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Abstract

Novel alkyne-bridged ferrocenophanes [fc{CO₂(CH₂)_nC≡}₂] (2a: n = 2; 2b: n = 3) were synthesized from the corresponding terminal diacetylenic ferrocenes [fc{CO₂(CH₂)_nC≡CH}₂] (1a: n = 2; 1b: n = 3) through ring-closing alkyne metathesis (RCAM) utilizing the highly effective molybdenum catalyst [MesC≡Mo{OC(CF₃)₂CH₃}₃] (MoF6; Mes = 2,4,6-trimethylphenyl). The metathesis reaction occurs in short time with high yields whilst giving full conversion of the terminal alkynes. Furthermore, the solvent dependant reactivity of 2a towards Ag(SbF₆) is investigated, leading to oxidation and formation of the ferrocenium hexafluoroantimonate 4 in dichloromethane, whereas the silver(I) coordination polymer 5 was isolated from THF solution.

Keywords: Alkyne metathesis; terminal alkynes; ferrocene; molybdenum; homogeneous catalysis

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Bittner, C.; Bockfeld, D.; Tamm, M. Beilstein Arch. 2019, 201971. doi:10.3762/bxiv.2019.71.v1

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Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

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