Reductive Denitrogenation of Six‐membered Cyclic Nitronates to Densely Substituted Dihydrofurans with Raney® Nickel/AcOH System

Reductive Denitrogenation of Six‐membered Cyclic Nitronates to Densely Substituted Dihydrofurans with Raney® Nickel/AcOH System Full article

Journal

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

Output data

Year: 2023, Volume: 365, Number: 17, Pages: 2850-2857 Pages count : 8 DOI: 10.1002/adsc.202300573

Authors

Pospelov Evgeny ¹ , Zhirov Alexander ^2,3 , Kamidolla Baglan ^4,3 , Sukhorukov Alexey ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, RUSSIAN FEDERATION
2	Department of Chemistry M. V. Lomonosov Moscow State University 119991 Leninskie gory, 1, str. 3 Moscow Russia
3	N. D. Zelinsky Institute of Organic Chemistry 119991 Leninsky prospect, 47 Moscow Russia
4	D. Mendeleev University of Chemical Technology of Russia 125047 Miusskaya sq., 9 Moscow Russia

A protocol for the synthesis of 2,3-dihydrofurans by reductive denitrogenation/ring contraction of 6-membered cyclic nitronates was developed. The process utilizes cheap Raney® nickel both as catalyst and stoichiometric agent without the need for high-pressure equipment. The products are formed in high purity and column chromatography is often not required. Studies on the substrate scope, functional group tolerance, and mechanism were performed. The developed approach provides a straightforward two-step access to densely substituted 2,3-dihydrofurans from nitrostyrenes and alkenes.

Pospelov E. , Zhirov A. , Kamidolla B. , Sukhorukov A.
Reductive Denitrogenation of Six‐membered Cyclic Nitronates to Densely Substituted Dihydrofurans with Raney® Nickel/AcOH System
Advanced Synthesis & Catalysis. 2023. V.365. N17. P.2850-2857. DOI: 10.1002/adsc.202300573 WOS Scopus OpenAlex

Web of science:	WOS:001038378400001
Scopus:	2-s2.0-85166215323
OpenAlex:	W4384497903

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OpenAlex	5
Scopus	5
Web of science	5