Z-selective dimerization of terminal alkynes by a (PNNP)FeII complex

Jeremiah E. Stevens; Justin D. Miller; Matthew C. Fitzsimmons; Curtis E. Moore; Christine M. Thomas

doi:10.1039/D4CC00469H

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Z-selective dimerization of terminal alkynes by a (PNNP)Fe^II complex†

Jeremiah E. Stevens,

^a Justin D. Miller,^a Matthew C. Fitzsimmons,^a Curtis E. Moore

^a and Christine M. Thomas

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry and Biochemistry, The Ohio State University, 100 W. 18th Ave., Columbus, OH 43210, USA
E-mail: thomasc@chemistry.ohio-state.edu

Abstract

A tetradentate bis(amido)bis(phosphine) Fe^II complex, (PNNP)Fe, is shown to activate the terminal C–H bond of aryl alkynes across its Fe–N_amide bonds. (PNNP)Fe is also shown to catalytically dimerize terminal aryl alkynes to produce 1,3-enynes with Z : E ratios as high as 96 : 4 with yields up to 95% and loadings as low as 1 mol% at 30 °C in 2 h. A plausible metal–ligand cooperative mechanism invoking a vinylidene intermediate is proposed.

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Article information

DOI: https://doi.org/10.1039/D4CC00469H
Article type: Communication
Submitted: 30 Jan 2024
Accepted: 07 Apr 2024
First published: 19 Apr 2024

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Chem. Commun., 2024, Advance Article

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Z-selective dimerization of terminal alkynes by a (PNNP)Fe^II complex

J. E. Stevens, J. D. Miller, M. C. Fitzsimmons, C. E. Moore and C. M. Thomas, Chem. Commun., 2024, Advance Article , DOI: 10.1039/D4CC00469H

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