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Front Cover: Synthesis of 3‐(Trifluoromethyl)indoles by Oxidative Cyclization of o ‐Sulfonamido‐α‐(trifluoromethyl)styrenes (Asian J. Org. Chem. 5/2019)
Author(s) -
Fujita Takeshi,
Ide Keisuke,
Jankins Tanner C.,
Nojima Tomoya,
Ichikawa Junji
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900268
Subject(s) - trifluoromethyl , chemistry , deprotonation , medicinal chemistry , indole test , intramolecular force , front cover , organic chemistry , cover (algebra) , ion , mechanical engineering , alkyl , engineering
3‐(Trifluoromethyl)indoles were successfully synthesized via oxidative cyclization through intramolecular C−H/N−H coupling reactions of α‐(trifluoromethyl)styrenes bearing a sulfonamido group at the ortho ‐position, which were promoted by cerium(IV) ammonium nitrate (CAN). This reaction proceeds via a radical 5‐ endo‐trig cyclization involving two sets of Ce‐mediated one‐electron oxidation followed by deprotonation. This protocol uses a relatively cheap fluorine‐containing compound (CF 3 CBr=CH 2 ) as a starting material and allows the installation of an indole framework and a trifluoromethyl group. More information can be found in the Communication by Junji Ichikawa et al. on page 637 in Issue 5, 2019 (DOI: 10.1002/ajoc.201900061).