Ruthenium-Catalyzed Dehydrogenative Intermolecular O-H/Si-H/C-H Silylation: Synthesis of (E)-Alkenyl Silyl-Ether and Silyl-Ether Heterocycle

Ziwei Huang; Qiao Lin; Jiefang Li; Shanshan Xu; Shaohuan Lv; Feng Xie; Jun Wang; Bin Li

doi:10.3390/molecules28207186

Ruthenium-Catalyzed Dehydrogenative Intermolecular O-H/Si-H/C-H Silylation: Synthesis of (E)-Alkenyl Silyl-Ether and Silyl-Ether Heterocycle

Ziwei Huang, Qiao Lin, Jiefang Li, Shanshan Xu, Shaohuan Lv, Feng Xie^*, Jun Wang, Bin Li^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

1 Citation (Scopus)

Abstract

Selective dehydrogenative silylation is one of the most valuable tools for synthesizing organosilicon compounds. In this study, a regio- and stereoselective ruthenium-catalyzed dehydrogenative intermolecular silylation was firstly developed to access (E)-alkenyl silyl-ether derivatives and silyl-ether heterocycles with good functional group tolerance. Furthermore, two pathways for RuH₂(CO)(PPh₃)₃/NBE-catalyzed dehydrogenative intermolecular silylation of alcohols and alkenes as well as intermolecular silylation of naphthol derivatives were investigated with H₂SiEt₂ as the hydrosilane reagent.

Original language	English
Article number	7186
Number of pages	13
Journal	Molecules
Volume	28
Issue number	20
DOIs	https://doi.org/10.3390/molecules28207186
Publication status	Published - 2 Oct 2023

User-Defined Keywords

C-H activation
dehydrogenative coupling
ruthenium catalysis
silyl-ether
silylation

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/molecules28207186

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title = "Ruthenium-Catalyzed Dehydrogenative Intermolecular O-H/Si-H/C-H Silylation: Synthesis of (E)-Alkenyl Silyl-Ether and Silyl-Ether Heterocycle",

abstract = "Selective dehydrogenative silylation is one of the most valuable tools for synthesizing organosilicon compounds. In this study, a regio- and stereoselective ruthenium-catalyzed dehydrogenative intermolecular silylation was firstly developed to access (E)-alkenyl silyl-ether derivatives and silyl-ether heterocycles with good functional group tolerance. Furthermore, two pathways for RuH2(CO)(PPh3)3/NBE-catalyzed dehydrogenative intermolecular silylation of alcohols and alkenes as well as intermolecular silylation of naphthol derivatives were investigated with H2SiEt2 as the hydrosilane reagent.",

keywords = "C-H activation, dehydrogenative coupling, ruthenium catalysis, silyl-ether, silylation",

author = "Ziwei Huang and Qiao Lin and Jiefang Li and Shanshan Xu and Shaohuan Lv and Feng Xie and Jun Wang and Bin Li",

note = "Funding Information: This research was funded the Foundation of the Department of Education of Guangdong Province (No: 2021ZDZX2045), the Foundation of Wuyi University (No: 2021WGALH06), the Foundation of Graduate Education Innovation Plan of Guangdong Province (No: YJS-JGXM-21-03, 2021JGXM111), and the Science and Technology Planning Project of Guangdong Province (2021B1212040016). Publisher Copyright: {\textcopyright} 2023 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2023",

month = oct,

day = "2",

doi = "10.3390/molecules28207186",

language = "English",

volume = "28",

journal = "Molecules",

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T1 - Ruthenium-Catalyzed Dehydrogenative Intermolecular O-H/Si-H/C-H Silylation

T2 - Synthesis of (E)-Alkenyl Silyl-Ether and Silyl-Ether Heterocycle

AU - Huang, Ziwei

AU - Lin, Qiao

AU - Li, Jiefang

AU - Xu, Shanshan

AU - Lv, Shaohuan

AU - Xie, Feng

AU - Wang, Jun

AU - Li, Bin

N1 - Funding Information: This research was funded the Foundation of the Department of Education of Guangdong Province (No: 2021ZDZX2045), the Foundation of Wuyi University (No: 2021WGALH06), the Foundation of Graduate Education Innovation Plan of Guangdong Province (No: YJS-JGXM-21-03, 2021JGXM111), and the Science and Technology Planning Project of Guangdong Province (2021B1212040016). Publisher Copyright: © 2023 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2023/10/2

Y1 - 2023/10/2

N2 - Selective dehydrogenative silylation is one of the most valuable tools for synthesizing organosilicon compounds. In this study, a regio- and stereoselective ruthenium-catalyzed dehydrogenative intermolecular silylation was firstly developed to access (E)-alkenyl silyl-ether derivatives and silyl-ether heterocycles with good functional group tolerance. Furthermore, two pathways for RuH2(CO)(PPh3)3/NBE-catalyzed dehydrogenative intermolecular silylation of alcohols and alkenes as well as intermolecular silylation of naphthol derivatives were investigated with H2SiEt2 as the hydrosilane reagent.

AB - Selective dehydrogenative silylation is one of the most valuable tools for synthesizing organosilicon compounds. In this study, a regio- and stereoselective ruthenium-catalyzed dehydrogenative intermolecular silylation was firstly developed to access (E)-alkenyl silyl-ether derivatives and silyl-ether heterocycles with good functional group tolerance. Furthermore, two pathways for RuH2(CO)(PPh3)3/NBE-catalyzed dehydrogenative intermolecular silylation of alcohols and alkenes as well as intermolecular silylation of naphthol derivatives were investigated with H2SiEt2 as the hydrosilane reagent.

KW - C-H activation

KW - dehydrogenative coupling

KW - ruthenium catalysis

KW - silyl-ether

KW - silylation

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U2 - 10.3390/molecules28207186

DO - 10.3390/molecules28207186

M3 - Journal article

C2 - 37894665

AN - SCOPUS:85175045257

SN - 1420-3049

VL - 28

JO - Molecules

JF - Molecules

IS - 20

M1 - 7186

ER -

Ruthenium-Catalyzed Dehydrogenative Intermolecular O-H/Si-H/C-H Silylation: Synthesis of (E)-Alkenyl Silyl-Ether and Silyl-Ether Heterocycle

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