Ruthenium-Catalyzed Regioselective 1,2-Hydrosilylation of N-Heteroarenes

Xinyuan Ma; Manoj Vasisht Mane; Luigi Cavallo; Steven Patrick Nolan

doi:10.1002/ejoc.202201466

Ruthenium-Catalyzed Regioselective 1,2-Hydrosilylation of N-Heteroarenes

Xinyuan Ma, Manoj Vasisht Mane, Luigi Cavallo, Steven Patrick Nolan

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

3 Scopus citations

Abstract

An efficient method for the regioselective 1,2-hydrosilylation of N-heteroarenes is reported utilizing silanes as the hydride donor. The ruthenium complex [RuCl(PPh3)2(η5-(3-phenylindenylidene))], a versatile catalyst is, for the first time, employed in this catalytic reaction. The catalyst displays high catalytic efficiency at low loading and operates under mild conditions. This catalytic approach showcases high compatibility and regioselectivity with quinolines bearing different substituents and related N- heterocyclic compounds. The mechanism of this transformation was probed by performing stoichiometric reactions and examined using DFT calculations.

Original language	English (US)
Journal	European Journal of Organic Chemistry
DOIs	https://doi.org/10.1002/ejoc.202201466
State	Published - Jan 27 2023

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry

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10.1002/ejoc.202201466

https://repository.kaust.edu.sa/bitstream/10754/687340/1/Eur%20J%20Org%20Chem%20-%202023%20-%20Ma%20-%20Ruthenium%e2%80%90Catalyzed%20Regioselective%201%202%e2%80%90Hydrosilylation%20of%20N%e2%80%90Heteroarenes_removed.pdf

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@article{7f228d84f2d54358bba8654e241f80ae,

title = "Ruthenium-Catalyzed Regioselective 1,2-Hydrosilylation of N-Heteroarenes",

abstract = "An efficient method for the regioselective 1,2-hydrosilylation of N-heteroarenes is reported utilizing silanes as the hydride donor. The ruthenium complex [RuCl(PPh3)2(η5-(3-phenylindenylidene))], a versatile catalyst is, for the first time, employed in this catalytic reaction. The catalyst displays high catalytic efficiency at low loading and operates under mild conditions. This catalytic approach showcases high compatibility and regioselectivity with quinolines bearing different substituents and related N- heterocyclic compounds. The mechanism of this transformation was probed by performing stoichiometric reactions and examined using DFT calculations.",

author = "Xinyuan Ma and Mane, {Manoj Vasisht} and Luigi Cavallo and Nolan, {Steven Patrick}",

note = "KAUST Repository Item: Exported on 2023-01-30 Acknowledgements: We gratefully acknowledge VLAIO (SBO project CO2PERATE). The Special Research Fund (BOF) of Ghent University is also acknowledged (starting and senior grants to SPN)as is the FWO(G0A6823N). XM thanks the CSC for a PhD fellowship. We are grateful to Nikolaos V. Tzouras for helpful discussions and with assistance in manuscript preparation. MVM, LC acknowledge King Abdullah University of Science and Technology (KAUST) for Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.",

year = "2023",

month = jan,

day = "27",

doi = "10.1002/ejoc.202201466",

language = "English (US)",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Ruthenium-Catalyzed Regioselective 1,2-Hydrosilylation of N-Heteroarenes

AU - Ma, Xinyuan

AU - Mane, Manoj Vasisht

AU - Cavallo, Luigi

AU - Nolan, Steven Patrick

N1 - KAUST Repository Item: Exported on 2023-01-30 Acknowledgements: We gratefully acknowledge VLAIO (SBO project CO2PERATE). The Special Research Fund (BOF) of Ghent University is also acknowledged (starting and senior grants to SPN)as is the FWO(G0A6823N). XM thanks the CSC for a PhD fellowship. We are grateful to Nikolaos V. Tzouras for helpful discussions and with assistance in manuscript preparation. MVM, LC acknowledge King Abdullah University of Science and Technology (KAUST) for Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.

PY - 2023/1/27

Y1 - 2023/1/27

N2 - An efficient method for the regioselective 1,2-hydrosilylation of N-heteroarenes is reported utilizing silanes as the hydride donor. The ruthenium complex [RuCl(PPh3)2(η5-(3-phenylindenylidene))], a versatile catalyst is, for the first time, employed in this catalytic reaction. The catalyst displays high catalytic efficiency at low loading and operates under mild conditions. This catalytic approach showcases high compatibility and regioselectivity with quinolines bearing different substituents and related N- heterocyclic compounds. The mechanism of this transformation was probed by performing stoichiometric reactions and examined using DFT calculations.

AB - An efficient method for the regioselective 1,2-hydrosilylation of N-heteroarenes is reported utilizing silanes as the hydride donor. The ruthenium complex [RuCl(PPh3)2(η5-(3-phenylindenylidene))], a versatile catalyst is, for the first time, employed in this catalytic reaction. The catalyst displays high catalytic efficiency at low loading and operates under mild conditions. This catalytic approach showcases high compatibility and regioselectivity with quinolines bearing different substituents and related N- heterocyclic compounds. The mechanism of this transformation was probed by performing stoichiometric reactions and examined using DFT calculations.

UR - http://hdl.handle.net/10754/687340

UR - https://onlinelibrary.wiley.com/doi/10.1002/ejoc.202201466

U2 - 10.1002/ejoc.202201466

DO - 10.1002/ejoc.202201466

M3 - Article

SN - 1434-193X

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

Ruthenium-Catalyzed Regioselective 1,2-Hydrosilylation of N-Heteroarenes

Abstract

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