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

ABSTRACT:

 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

DOI: 10.1021/acs.joc.8b02766

全文链接：http://dx.doi.org/10.1021/acs.joc.8b02766