Synthesis of Aryl Trimethylstannane via BF 3 ·OEt 2 ‑Mediated Cross-Coupling of Hexaalkyl Distannane Reagent with Aryl Triazene at Room Temperature
Shuai Mao†, Zhengkai Chen‡, Lu Wang†, Daulat Bikram Khadka§, Minhang Xin†,Pengfei Li∥*, and San-Qi Zhang†*
†Department of Medicinal Chemistry, School of Pharmacy, Xi’an Jiaotong University, Xi’an 710061, China
‡Department of Chemistry, Zhejiang Sci-Tech University, Zhejiang, Hangzhou 310018, China
∥Frontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an, Shaanxi 710054, China
§Department of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, Michigan 48109, United States
BF 3·OEt 2 -mediated cross-coupling of (SnMe 3 ) 2 with aryl triazene o ﬀ ers a new strategy for the synthesis of aryl stannane. A variety of synthetically useful aryl trimethylstannanes were produced in moderate to good yields with this metal-free approach. One-pot sequential Stille cross-coupling with di ﬀ erent aryl bromides provides a short entry to both symmetrical and unsymmetrical biaryl compounds.
J. Org. Chem. 2019, 84, 463−471