Palladium-Catalyzed Silacyclization of (Hetero)Arenes with a Tetrasilane Reagent through Twofold C-H Activation

Dingyi Wang; Mingjie Li; Xiangyang Chen; Minyan Wang; Yong Liang; Yue Zhao; Kendall N Houk; Zhuangzhi Shi

doi:10.1002/anie.202015117

Palladium-Catalyzed Silacyclization of (Hetero)Arenes with a Tetrasilane Reagent through Twofold C-H Activation

Angew Chem Int Ed Engl. 2021 Mar 22;60(13):7066-7071. doi: 10.1002/anie.202015117. Epub 2021 Feb 24.

Authors

Dingyi Wang¹, Mingjie Li¹, Xiangyang Chen², Minyan Wang¹, Yong Liang¹, Yue Zhao¹, Kendall N Houk², Zhuangzhi Shi¹

Affiliations

¹ State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
² Department of Chemistry and Biochemistry, University of California, Los Angeles, CA, 90095, USA.

PMID: 33377224
DOI: 10.1002/anie.202015117

Abstract

The use of an operationally convenient and stable silicon reagent (octamethyl-1,4-dioxacyclohexasilane, ODCS) for the selective silacyclization of (hetero)arenes via twofold C-H activation is reported. This method is compatible with N-containing heteroarenes such as indoles and carbazoles of varying complexity. The ODCS reagent can also be utilized for silacyclization of other types of substrates, including tertiary phosphines and aryl halides. A series of mechanistic experiments and density functional theory (DFT) calculations were used to investigate the preferred pathway for this twofold C-H activation process.

Keywords: ODCS; heteroarenes; palladium; silacyclization; silylation.

Abstract

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