Green, Catalyst-Free Reaction of Indoles with β-Fluoro-β-nitrostyrenes in Water

Green, Catalyst-Free Reaction of Indoles with β-Fluoro-β-nitrostyrenes in Water Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2018, Volume: 2018, Number: 27-28, Pages: 3816-3825 Pages count : 10 DOI: 10.1002/ejoc.201800385

Authors

Aldoshin Alexander S. ¹ , Tabolin Andrey A. ² , Ioffe Sema L. ² , Nenajdenko Valentine G. ¹

Affiliations

1	Department of Chemistry; Lomonosov Moscow State University; 11999 Moscow Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry; Russian Academy of Sciences; Leninsky prosp. 47 119991 Moscow Russian Federation

The reaction of 2-fluoro-2-nitrostyrenes with various indoles was investigated. We found that the reaction proceeds as a Michael addition in a highly regioselective manner to form 3-(1-aryl-2-fluoro-2-nitroethyl)-1H-indoles. Thus, a green and catalyst-free synthesis of these compounds was developed using water as a reaction medium. The high effectiveness of this approach was demonstrated through the preparation of target products in up to 92 % isolated yield. Subsequent reduction of the nitro group was investigated. We found that due to the instability of the intermediate α-fluoro amines, the reduction led to non-fluorinated tryptamine derivatives.

Aldoshin A.S. , Tabolin A.A. , Ioffe S.L. , Nenajdenko V.G.
Green, Catalyst-Free Reaction of Indoles with β-Fluoro-β-nitrostyrenes in Water
European Journal of Organic Chemistry. 2018. V.2018. N27-28. P.3816-3825. DOI: 10.1002/ejoc.201800385 WOS Scopus OpenAlex

≡ Web of science:	WOS:000439775200028
≡ Scopus:	2-s2.0-85050389978
≡ OpenAlex:	W2802244907