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

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

doi:10.71267/mencom.7763

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

Egor D Tokhtobin ^{1, 2}

Egor D Tokhtobin

,

Andrei K Zaitsev ²

Andrei K Zaitsev

,

Rinat Faritovich Salikov ²

Rinat Faritovich Salikov

,

Alexander Yuryevich Belyy ²

Alexander Yuryevich Belyy

,

Yury Vasil'evich Tomilov ²

Yury Vasil'evich Tomilov

0000-0002-3433-7571

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

10.71267/mencom.7763

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Published 2025-07-17

Communication , Volume 35, Issue 5, 524-526

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Tokhtobin E. D. et al. Protic additives in aprotic solvent: a tool to improve sodium borohydride reductions of C-C bonds // Mendeleev Communications. 2025. Vol. 35. No. 5. pp. 524-526.

GOST all authors (up to 50) Copy

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. Vol. 35. No. 5. pp. 524-526.

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TY - JOUR

DO - 10.71267/mencom.7763

UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7763

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

T2 - Mendeleev Communications

AU - Tokhtobin, Egor D

AU - Zaitsev, Andrei K

AU - Salikov, Rinat Faritovich

AU - Belyy, Alexander Yuryevich

AU - Tomilov, Yury Vasil'evich

PY - 2025

DA - 2025/07/17

PB - Mendeleev Communications

SP - 524-526

IS - 5

VL - 35

ER -

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@article{2025_Tokhtobin,

author = {Egor D Tokhtobin and Andrei K Zaitsev and Rinat Faritovich Salikov and Alexander Yuryevich Belyy and Yury Vasil'evich Tomilov},

title = {Protic additives in aprotic solvent: a tool to improve sodium borohydride reductions of C-C bonds},

journal = {Mendeleev Communications},

year = {2025},

volume = {35},

publisher = {Mendeleev Communications},

month = {Jul},

url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7763},

number = {5},

pages = {524--526},

doi = {10.71267/mencom.7763}

}

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Tokhtobin, Egor D., et al. “Protic additives in aprotic solvent: a tool to improve sodium borohydride reductions of C-C bonds.” Mendeleev Communications, vol. 35, no. 5, Jul. 2025, pp. 524-526. https://mendcomm.colab.ws/publications/10.71267/mencom.7763.

Keywords

aromaticity

cycloheptatrienes

cyclopropenones.

electrocyclic reactions

Favorskii reaction

Nazarov reaction

olefins

reduction

sodium borohydride

transition state aromaticity

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.

Funders

Russian Science Foundation

23-73-10181

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