Alkene, Bromide, and ROH – How To Achieve Selectivity? Electrochemical Synthesis of Bromohydrins and Their Ethers

Alkene, Bromide, and ROH – How To Achieve Selectivity? Electrochemical Synthesis of Bromohydrins and Their Ethers Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2021, Volume: 363, Number: 12, Pages: 3070-3078 Pages count : 9 DOI: 10.1002/adsc.202100161

Authors

Bityukov Oleg Vadimovich ^1,2 , Vil Vera ^1,2 , Nikishin Gennady ¹ , Terent'ev Alexander ^1,2

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	All-Russian Research Institute for Phytopathology, B. Vyazyomy, Moscow Region, 143050 Russian Federation

Bromohydrins and their ethers were electrochemically synthesized via hydroxy- and alkoxybromination of alkenes using potassium bromide and water or alcohols. High selectivity of bromohydrins formation was achieved only with the use of DMSO as the solvent and an acid as the additive. The proposed combination of starting reagents, additives, and solvents allowed to form bromohydrins or their ethers selectively despite the variety of side-products (epoxides, dibromides, diols). Bromohydrins were obtained in high yields, up to 96%, with a broad substrate scope in an undivided electrochemical cell equipped with glassy carbon and platinum electrodes at high current density.

Bityukov O.V. , Vil V. , Nikishin G. , Terent'ev A.
Alkene, Bromide, and ROH – How To Achieve Selectivity? Electrochemical Synthesis of Bromohydrins and Their Ethers
Advanced Synthesis & Catalysis. 2021. V.363. N12. P.3070-3078. DOI: 10.1002/adsc.202100161 WOS Scopus OpenAlex

Web of science:	WOS:000647955100001
Scopus:	2-s2.0-85105340484
OpenAlex:	W3159728489

DB	Citing
OpenAlex	26
Web of science	25
Scopus	24