Communications

Protic additives in aprotic solvent: a tool to improve sodium borohydride reductions of C–C bonds

E. D. Tokhtobin^ab, A. K. Zaitsev^a, R. F. Salikov^a, A. Yu. Belyy^a, Yu. V. Tomilov<sup>a

a</sup> N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
^b Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation

Abstract: 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.

Keywords: sodium borohydride, reduction, aromaticity, Favorskii reaction, Nazarov reaction, electrocyclic reactions, transition state aromaticity, olefins, cycloheptatrienes, cyclopropenones.

Received: 13.03.2025
Accepted: 22.04.2025

Language: English

DOI: 10.71267/mencom.7763

Bibliographic databases:

•