One-Pot Rapid Access to Benzyl Silanes, Germanes, and Stannanes from Toluenes Mediated by a LiN(SiMe3)2/CsCl System

Yaqi Yuan; Yuanyun Gu; Yan-En Wang; Jiali Zheng; Jiaying Ji; Dan Xiong; Fei Xue; Jianyou Mao

doi:10.1021/acs.joc.2c01612

One-Pot Rapid Access to Benzyl Silanes, Germanes, and Stannanes from Toluenes Mediated by a LiN(SiMe₃)₂/CsCl System

J Org Chem. 2022 Nov 4;87(21):13907-13918. doi: 10.1021/acs.joc.2c01612. Epub 2022 Oct 25.

Authors

Yaqi Yuan¹, Yuanyun Gu¹, Yan-En Wang², Jiali Zheng¹, Jiaying Ji¹, Dan Xiong¹, Fei Xue³, Jianyou Mao¹

Affiliations

¹ School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. China.
² College of Science, Hebei Agricultural University, Baoding 071000, P. R. China.
³ Institute of Material Physics & Chemistry, College of Science, Nanjing Forestry University, Nanjing 210037, P. R. China.

PMID: 36282491
DOI: 10.1021/acs.joc.2c01612

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.