Synthesis of Iron Hydride Complexes Relevant to Hydrogen Isotope Exchange in Pharmaceuticals

Renyuan Pony Yu; Jonathan M. Darmon; Scott P. Semproni; Zoë R. Turner; Paul J. Chirik

doi:10.1021/acs.organomet.7b00398

Synthesis of Iron Hydride Complexes Relevant to Hydrogen Isotope Exchange in Pharmaceuticals

Renyuan Pony Yu, Jonathan M. Darmon, Scott P. Semproni, Zoë R. Turner, Paul J. Chirik

Chemistry

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

Addition of H₂ gas to the bis(arylimidazolin-2-ylidene)pyridine iron bis(dinitrogen) complex (H₄-^iPrCNC)Fe(N₂)₂ resulted in facile oxidative addition of the H-H bond to yield a mixture of (H₄-^iPrCNC)FeH₄ and trans-(H₄-^iPrCNC)FeH₂(N₂), depending on the partial pressures of H₂ and N₂. Both iron hydride complexes were characterized by X-ray diffraction and proved relevant to the catalytic hydrogen isotope exchange of arene C(sp²)-H bonds. Activation of the benzene-d₆ solvent at ambient temperature produced deuterated isotologues of both compounds that exhibit large isotopic perturbation of resonances in the hydride signals.

Original language	English (US)
Pages (from-to)	4341-4343
Number of pages	3
Journal	Organometallics
Volume	36
Issue number	22
DOIs	https://doi.org/10.1021/acs.organomet.7b00398
State	Published - Nov 27 2017

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/acs.organomet.7b00398

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title = "Synthesis of Iron Hydride Complexes Relevant to Hydrogen Isotope Exchange in Pharmaceuticals",

abstract = "Addition of H2 gas to the bis(arylimidazolin-2-ylidene)pyridine iron bis(dinitrogen) complex (H4-iPrCNC)Fe(N2)2 resulted in facile oxidative addition of the H-H bond to yield a mixture of (H4-iPrCNC)FeH4 and trans-(H4-iPrCNC)FeH2(N2), depending on the partial pressures of H2 and N2. Both iron hydride complexes were characterized by X-ray diffraction and proved relevant to the catalytic hydrogen isotope exchange of arene C(sp2)-H bonds. Activation of the benzene-d6 solvent at ambient temperature produced deuterated isotologues of both compounds that exhibit large isotopic perturbation of resonances in the hydride signals.",

author = "Yu, {Renyuan Pony} and Darmon, {Jonathan M.} and Semproni, {Scott P.} and Turner, {Zo{\"e} R.} and Chirik, {Paul J.}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.organomet.7b00398",

language = "English (US)",

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T1 - Synthesis of Iron Hydride Complexes Relevant to Hydrogen Isotope Exchange in Pharmaceuticals

AU - Yu, Renyuan Pony

AU - Darmon, Jonathan M.

AU - Semproni, Scott P.

AU - Turner, Zoë R.

AU - Chirik, Paul J.

PY - 2017/11/27

Y1 - 2017/11/27

N2 - Addition of H2 gas to the bis(arylimidazolin-2-ylidene)pyridine iron bis(dinitrogen) complex (H4-iPrCNC)Fe(N2)2 resulted in facile oxidative addition of the H-H bond to yield a mixture of (H4-iPrCNC)FeH4 and trans-(H4-iPrCNC)FeH2(N2), depending on the partial pressures of H2 and N2. Both iron hydride complexes were characterized by X-ray diffraction and proved relevant to the catalytic hydrogen isotope exchange of arene C(sp2)-H bonds. Activation of the benzene-d6 solvent at ambient temperature produced deuterated isotologues of both compounds that exhibit large isotopic perturbation of resonances in the hydride signals.

AB - Addition of H2 gas to the bis(arylimidazolin-2-ylidene)pyridine iron bis(dinitrogen) complex (H4-iPrCNC)Fe(N2)2 resulted in facile oxidative addition of the H-H bond to yield a mixture of (H4-iPrCNC)FeH4 and trans-(H4-iPrCNC)FeH2(N2), depending on the partial pressures of H2 and N2. Both iron hydride complexes were characterized by X-ray diffraction and proved relevant to the catalytic hydrogen isotope exchange of arene C(sp2)-H bonds. Activation of the benzene-d6 solvent at ambient temperature produced deuterated isotologues of both compounds that exhibit large isotopic perturbation of resonances in the hydride signals.

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Synthesis of Iron Hydride Complexes Relevant to Hydrogen Isotope Exchange in Pharmaceuticals

Abstract

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