One-Pot Rapid Access to Benzyl Silanes, Germanes, and Stannanes from Toluenes Mediated by a LiN(SiMe<sub>3</sub>)<sub>2</sub>/CsCl System
Yaqi Yuan, Yuanyun Gu, Yan‐En Wang, Jiali Zheng, Jiaying Ji, Dan Xiong, Fei Xue, Jianyou Mao
Abstract
Organo-silanes, germanes, and stannanes are considered to be conducive to the development of cross-coupling reactions because they are stable, nontoxic, and easy to handle. Using feedstock toluenes, one-pot direct benzylic C–H silylations, germylations, and stannylations are developed. Simply combining toluenes, LiN(SiMe3)2/CsCl, and R3MCl (M = Si, Ge, Sn) generates a diverse array of bench-stable benzyl silanes, germanes, and stannanes (38 examples, 53–90% yields). The syntheses developed here are easy to access on scale.
Topics & Concepts
SilanesChemistryCoupling (piping)Organic chemistryMaterials scienceMetallurgySilaneOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods