Front Cover: Synthesis of 3‐(Trifluoromethyl)indoles by Oxidative Cyclization of o‐Sulfonamido‐α‐(trifluoromethyl)styrenes (Asian J. Org. Chem. 5/2019). Issue 5 (10th May 2019)

• Record Type: Journal Article
• Authors: Fujita, Takeshi; Ide, Keisuke; Jankins, Tanner C.; Nojima, Tomoya; Ichikawa, Junji
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 5(2019)
• Page Start: 564
• Page End: 564
• Publication Date: 2019-05-10
• Subjects: fluorine -- indole -- cyclization -- oxidation -- radical; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900268
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract : 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 (CF3 CBr=CH2 ) 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. onpage 637 in Issue 5, 2019 (DOI:10.1002/ajoc.201900061 ).