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, K. N. Houk, Zhuangzhi Shi
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.
Topics & Concepts
ReagentChemistryPalladiumCatalysisHalideArylCombinatorial chemistryDensity functional theoryOrganic chemistryComputational chemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistry