Tetrachloromethane as an editable all-carbon quaternary source.
basic_science · Level V
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- Record sourced from PubMed, PMID 41501045.
- Also identified by DOI 10.1038/s41467-025-68224-z and PMC identifier 12891700.
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Abstract
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.