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Green, Catalyst‐Free Reaction of Indoles with β‐Fluoro‐β‐nitrostyrenes in Water
Author(s) -
Aldoshin Alexander S.,
Tabolin Andrey A.,
Ioffe Sema L.,
Nenajdenko Valentine G.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800385
Subject(s) - chemistry , tryptamine , catalysis , yield (engineering) , regioselectivity , nitro , organic chemistry , aryl , green chemistry , reaction conditions , michael reaction , combinatorial chemistry , medicinal chemistry , reaction mechanism , biochemistry , materials science , alkyl , metallurgy
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)‐1 H ‐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.