Organogermanium(II) Hydrides as a Source of Highly Soluble LiH

Jakub Tremmel; Jiří  Tydlitát; Libor  Dostál; Aleš  Růžička; Xavier Deraet; Jan Turek; Roman Jambor

doi:10.1002/chem.202000970

Organogermanium(II) Hydrides as a Source of Highly Soluble LiH

Jakub Tremmel, Jiří Tydlitát, Libor Dostál, Aleš Růžička, Xavier Deraet, Jan Turek, Roman Jambor

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Abstract

The reactions of monomeric C,N-chelated organogermanium(II) hydride L(H)Ge⋅BH₃ with organolithium salts RLi yielded lithium hydrogermanatoborates (Li(THF)₂{BH₃[L(H)GeR]})₂. Compound (Li(THF)₂{BH₃[L(H)GePh]})₂ was used as a source of LiH for the reduction of organic C=O or C=N bonds in nonpolar solvents accompanied by the elimination of a neutral complex L(Ph)Ge⋅BH₃. The interaction of (Li(THF)₂{BH₃[L(H)GePh]})₂ with the polar C=O bond was further investigated by computational studies revealing a plausible geometry of a pre-reactive intermediate. The experimental and theoretical studies suggest that, although the Li atom of (Li(THF)₂{BH₃[L(H)GePh]})₂ coordinates the C=O bond, the GeH fragment is the active species in the reduction reaction. Finally, benzaldehyde was reduced by a mixture of L(H)Ge⋅BH₃ with PhLi in nonpolar solvents.

Original language	English
Pages (from-to)	6070-6075
Number of pages	6
Journal	Chemistry - a European Journal
Volume	26
Issue number	27
DOIs	https://doi.org/10.1002/chem.202000970
Publication status	Published - 12 May 2020

Bibliographical note

Funding Information:
R.J. would like to acknowledge the Czech Science foundation (project 20‐10417S) for financial support. J.T. would like to acknowledge the financial support of the Research Foundation‐Flanders (FWO; Project No. 12Y7718N) and the computational resources and services provided by the Shared ICT Services Centre funded by the Vrije Universiteit Brussel, the Flemish Supercomputer Centre (VSC) and FWO. X.D. wishes to acknowledge the Vrije Universiteit Brussel for the Strategic Research Program.

Funding Information:
R.J. would like to acknowledge the Czech Science foundation (project 20-10417S) for financial support. J.T. would like to acknowledge the financial support of the Research Foundation-Flanders (FWO; Project No. 12Y7718N) and the computational resources and services provided by the Shared ICT Services Centre funded by the Vrije Universiteit Brussel, the Flemish Supercomputer Centre (VSC) and FWO. X.D. wishes to acknowledge the Vrije Universiteit Brussel for the Strategic Research Program.

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

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title = "Organogermanium(II) Hydrides as a Source of Highly Soluble LiH",

abstract = "The reactions of monomeric C,N-chelated organogermanium(II) hydride L(H)Ge⋅BH3 with organolithium salts RLi yielded lithium hydrogermanatoborates (Li(THF)2{BH3[L(H)GeR]})2. Compound (Li(THF)2{BH3[L(H)GePh]})2 was used as a source of LiH for the reduction of organic C=O or C=N bonds in nonpolar solvents accompanied by the elimination of a neutral complex L(Ph)Ge⋅BH3. The interaction of (Li(THF)2{BH3[L(H)GePh]})2 with the polar C=O bond was further investigated by computational studies revealing a plausible geometry of a pre-reactive intermediate. The experimental and theoretical studies suggest that, although the Li atom of (Li(THF)2{BH3[L(H)GePh]})2 coordinates the C=O bond, the GeH fragment is the active species in the reduction reaction. Finally, benzaldehyde was reduced by a mixture of L(H)Ge⋅BH3 with PhLi in nonpolar solvents.",

author = "Jakub Tremmel and Ji{\v r}{\'i} Tydlit{\'a}t and Libor Dost{\'a}l and Ale{\v s} Rů{\v z}i{\v c}ka and Xavier Deraet and Jan Turek and Roman Jambor",

note = "Funding Information: R.J. would like to acknowledge the Czech Science foundation (project 20‐10417S) for financial support. J.T. would like to acknowledge the financial support of the Research Foundation‐Flanders (FWO; Project No. 12Y7718N) and the computational resources and services provided by the Shared ICT Services Centre funded by the Vrije Universiteit Brussel, the Flemish Supercomputer Centre (VSC) and FWO. X.D. wishes to acknowledge the Vrije Universiteit Brussel for the Strategic Research Program. Funding Information: R.J. would like to acknowledge the Czech Science foundation (project 20-10417S) for financial support. J.T. would like to acknowledge the financial support of the Research Foundation-Flanders (FWO; Project No. 12Y7718N) and the computational resources and services provided by the Shared ICT Services Centre funded by the Vrije Universiteit Brussel, the Flemish Supercomputer Centre (VSC) and FWO. X.D. wishes to acknowledge the Vrije Universiteit Brussel for the Strategic Research Program. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2020",

month = may,

day = "12",

doi = "10.1002/chem.202000970",

language = "English",

volume = "26",

pages = "6070--6075",

journal = "Chemistry - a European Journal",

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T1 - Organogermanium(II) Hydrides as a Source of Highly Soluble LiH

AU - Tremmel, Jakub

AU - Tydlitát, Jiří

AU - Dostál, Libor

AU - Růžička, Aleš

AU - Deraet, Xavier

AU - Turek, Jan

AU - Jambor, Roman

N1 - Funding Information: R.J. would like to acknowledge the Czech Science foundation (project 20‐10417S) for financial support. J.T. would like to acknowledge the financial support of the Research Foundation‐Flanders (FWO; Project No. 12Y7718N) and the computational resources and services provided by the Shared ICT Services Centre funded by the Vrije Universiteit Brussel, the Flemish Supercomputer Centre (VSC) and FWO. X.D. wishes to acknowledge the Vrije Universiteit Brussel for the Strategic Research Program. Funding Information: R.J. would like to acknowledge the Czech Science foundation (project 20-10417S) for financial support. J.T. would like to acknowledge the financial support of the Research Foundation-Flanders (FWO; Project No. 12Y7718N) and the computational resources and services provided by the Shared ICT Services Centre funded by the Vrije Universiteit Brussel, the Flemish Supercomputer Centre (VSC) and FWO. X.D. wishes to acknowledge the Vrije Universiteit Brussel for the Strategic Research Program. Publisher Copyright: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/5/12

Y1 - 2020/5/12

N2 - The reactions of monomeric C,N-chelated organogermanium(II) hydride L(H)Ge⋅BH3 with organolithium salts RLi yielded lithium hydrogermanatoborates (Li(THF)2{BH3[L(H)GeR]})2. Compound (Li(THF)2{BH3[L(H)GePh]})2 was used as a source of LiH for the reduction of organic C=O or C=N bonds in nonpolar solvents accompanied by the elimination of a neutral complex L(Ph)Ge⋅BH3. The interaction of (Li(THF)2{BH3[L(H)GePh]})2 with the polar C=O bond was further investigated by computational studies revealing a plausible geometry of a pre-reactive intermediate. The experimental and theoretical studies suggest that, although the Li atom of (Li(THF)2{BH3[L(H)GePh]})2 coordinates the C=O bond, the GeH fragment is the active species in the reduction reaction. Finally, benzaldehyde was reduced by a mixture of L(H)Ge⋅BH3 with PhLi in nonpolar solvents.

AB - The reactions of monomeric C,N-chelated organogermanium(II) hydride L(H)Ge⋅BH3 with organolithium salts RLi yielded lithium hydrogermanatoborates (Li(THF)2{BH3[L(H)GeR]})2. Compound (Li(THF)2{BH3[L(H)GePh]})2 was used as a source of LiH for the reduction of organic C=O or C=N bonds in nonpolar solvents accompanied by the elimination of a neutral complex L(Ph)Ge⋅BH3. The interaction of (Li(THF)2{BH3[L(H)GePh]})2 with the polar C=O bond was further investigated by computational studies revealing a plausible geometry of a pre-reactive intermediate. The experimental and theoretical studies suggest that, although the Li atom of (Li(THF)2{BH3[L(H)GePh]})2 coordinates the C=O bond, the GeH fragment is the active species in the reduction reaction. Finally, benzaldehyde was reduced by a mixture of L(H)Ge⋅BH3 with PhLi in nonpolar solvents.

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U2 - 10.1002/chem.202000970

DO - 10.1002/chem.202000970

M3 - Article

VL - 26

SP - 6070

EP - 6075

JO - Chemistry - a European Journal

JF - Chemistry - a European Journal

SN - 0947-6539

IS - 27

ER -

Organogermanium(II) Hydrides as a Source of Highly Soluble LiH

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