Scholarlink

<p>Despite the widespread presence of all-carbon quaternary centers in natural products and bioactive compounds, a concise construction strategy remains very challenging. Herein, we introduce a highly controllable sequential dechlorination strategy of tetrachloromethane by means of relay catalysis with different photocatalysts of eosin Y, 1,2,3,5-tetrakis(carbazol-9-yl)−4,6-dicyanobenzene and Au<sub>2</sub>(µ-dcpm)<sub>2</sub>Cl<sub>2</sub>. Four C-Cl bonds in CCl<sub>4</sub> can undergo sequential, highly selective cleavage by combination of outer-sphere and inner-sphere crossover single electron transfer mechanism, enabling radical-addition reactions with a wide range of terminal alkenes to construct all-carbon quaternary centers in four steps with 17-38% yields. Furthermore, using 1,1-disubstituted styrene as the substrates, cyclopropanes bearing with challenging vicinal all-carbon quaternary centers are also successfully constructed from CCl<sub>4</sub> in two-pots three steps with moderate yields of 10-50%. This work suggests the possibility of tetrachloromethane as an editable C1 synthon to facilitate the construction of all-carbon quaternary centers.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Tetrachloromethane as an editable all-carbon quaternary source

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2026年1月7日

查看全文
  • Tingrui Li,
  • Zhi Liu,
  • Yulong Fu,
  • Hongliang Chen,
  • Jun Huang,
  • Yongxing Tang,
  • Jin Xie

摘要

Despite the widespread presence of all-carbon quaternary centers in natural products and bioactive compounds, a concise construction strategy remains very challenging. Herein, we introduce a highly controllable sequential dechlorination strategy of tetrachloromethane by means of relay catalysis with different photocatalysts of eosin Y, 1,2,3,5-tetrakis(carbazol-9-yl)−4,6-dicyanobenzene and Au2(µ-dcpm)2Cl2. Four C-Cl bonds in CCl4 can undergo sequential, highly selective cleavage by combination of outer-sphere and inner-sphere crossover single electron transfer mechanism, enabling radical-addition reactions with a wide range of terminal alkenes to construct all-carbon quaternary centers in four steps with 17-38% yields. Furthermore, using 1,1-disubstituted styrene as the substrates, cyclopropanes bearing with challenging vicinal all-carbon quaternary centers are also successfully constructed from CCl4 in two-pots three steps with moderate yields of 10-50%. This work suggests the possibility of tetrachloromethane as an editable C1 synthon to facilitate the construction of all-carbon quaternary centers.