Metal-free homo-/cross-anion-cation coupling of cyclic diaryl λ3-bromanes

作者：Wang, Yiwen; Tian, Ya-Nan; Ren, Shiyan; Zhu, Ruijie; Huang, Bin; Wen, Yanqiong; Li, Shiqing^*

来源：Organic Chemistry Frontiers, 2023, 10(3): 793-798.

DOI：10.1039/d2qo01406h

• SALTS
• AMINATION
• ARYLATION
• BROMONIUM
• STRATEGY

The homo anion-cation coupling of cyclic diaryl lambda(3)-bromanes/diarylbrominiums, which was not reported in previous reports, has been disclosed for the first time. The competition experiments indicate that the anion-cation coupling follows the nucleophilic ability of the anions: the higher the nucleophilicity, the higher the reactivity. Moreover, metal-free cross-coupling of cyclic diarylbrominium tosylates with primary/secondary/tertiary/cyclic/linear/natural alcohols, phenols, water and their deuterated forms under mild conditions has been developed, giving meta-functionalized biaryl motifs in high yields with broad substrate scope. Preliminary mechanistic studies show that the nucleophilic agent is the major proton source in the cross-anion-cation coupling, which is affected by its concentration.

• 单位
  桂林理工大学