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

Molecules. 2023 Oct 20;28(20):7186. doi: 10.3390/molecules28207186.

Authors

Ziwei Huang^{1

2}, Qiao Lin¹, Jiefang Li¹, Shanshan Xu¹, Shaohuan Lv¹, Feng Xie¹, Jun Wang³, Bin Li^{1

4}

Affiliations

¹ School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, China.
² Guangdong Wamo New Material Technology Co., Ltd., Jiangmen 529020, China.
³ Department of Chemistry, Hong Kong Baptist University, Hong Kong, China.
⁴ Guangdong Provincial Key Laboratory of Large Animal Models for Biomedicine, Wuyi University, Jiangmen 529020, China.

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.

Grants and funding

2021ZDZX2045/the Support of the Foundation of Department of Education of Guangdong Province