Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids

Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2019, Volume: 84, Number: 3, Pages: 1448-1460 Pages count : 13 DOI: 10.1021/acs.joc.8b02791

Authors

Bityukov Oleg V. ¹ , Matveeva Olesya K. ^2,1 , Vil’ Vera A. ¹ , Kokorekin Vladimir A. ^1,3 , Nikishin Gennady I. ¹ , Terent’ev Alexander O. ^2,1

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow 119991, Russian Federation
2	D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow 125047, Russian Federation
3	Sechenov First Moscow State Medical University, Trubetskaya st. 8-2, Moscow 119991, Russian Federation

The electrochemically induced cross-dehydrogenative C–O coupling of β-diketones and β-ketoesters (C–H reagents) with carboxylic acids (O–H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C–O coupling products in high yields, up to 92%, using DMSO as a solvent with a broad substrate scope in an undivided cell equipped with carbon and platinum electrodes at high current density. Electric current acts as a stoichiometric oxidant.

Bityukov O.V. , Matveeva O.K. , Vil’ V.A. , Kokorekin V.A. , Nikishin G.I. , Terent’ev A.O.
Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids
Journal of Organic Chemistry. 2019. V.84. N3. P.1448-1460. DOI: 10.1021/acs.joc.8b02791 WOS Scopus OpenAlex

≡ Web of science:	WOS:000457947800032
≡ Scopus:	2-s2.0-85060943929
≡ OpenAlex:	W2910429522