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

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

Journal

Mendeleev Communications
ISSN: 1364-551X , E-ISSN: 0959-9436

Output data

Year: 2025, Volume: 35, Number: 5, Pages: 524-526 Pages count : 3 DOI: 10.71267/mencom.7763

Authors

Tokhtobin Egor D ^1,2 , Zaitsev Andrei K ² , Salikov Rinat Faritovich ² , Belyy Alexander Yuryevich ² , Tomilov Yury Vasil'evich ²

Affiliations

1	Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation

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.

Tokhtobin E.D. , Zaitsev A.K. , Salikov R.F. , Belyy A.Y. , Tomilov Y.V.
Protic additives in aprotic solvent: a tool to improve sodium borohydride reductions of C-C bonds
Mendeleev Communications. 2025. V.35. N5. P.524-526. DOI: 10.71267/mencom.7763 WOS Scopus OpenAlex

≡ Web of science:	WOS:001544036400007
≡ Scopus:	2-s2.0-105011985757
≡ OpenAlex:	W4413065016