Protic additives in aprotic solvent: a tool to improve sodium borohydride reductions of C-C bonds
This study explores the reduction of electrophilic carbon--carbon double bonds using sodium borohydride in aqueous acetonitrile to effectively protonate reactive intermediate enolate anions, thereby mitigating unwanted polymerization processes. The reduction of strong Michael acceptors leads to the corresponding saturated (‘dihydro’) analogues. In cases of electron-poor cycloheptatrienes and proaromatic cyclopropenones the initial reduction is followed by either ring-contraction or ring-opening, respectively.
Authors
- А. В. Зайцев (ORCID: https://orcid.org/0000-0001-6448-2561)
- Yury Vasil'evich Tomilov (ORCID: https://orcid.org/0000-0002-3433-7571)
- Rinat Faritovich Salikov (ORCID: https://orcid.org/0000-0002-7901-600X)
- Alexander Yu. Belyy (ORCID: https://orcid.org/0000-0002-4948-6238)
- Egor D Tokhtobin
Institutions
- Russian Academy of Sciences (RU)
- D. Mendeleyev University of Chemical Technology of Russia (RU)
- N.D. Zelinsky Institute of Organic Chemistry (RU)
Publication Details
- Journal
- Mendeleev Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.71267/mencom.7763
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Russian Science Foundation