A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines. Issue 6 (19th January 2016)

• Record Type: Journal Article
• Authors: Ikeda, A.; Omote, M.; Kusumoto, K.; Komori, M.; Tarui, A.; Sato, K.; Ando, A.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 6(2016)
• Page Start: 2127
• Page End: 2133
• Publication Date: 2016-01-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02558c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A dramatic enhancing effect of InBr3 was observed towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylaniline with ( E )-trimethyl(3, 3, 3-trifluoroprop-1-enyl)silane. Abstract : The addition of InBr3 to the oxidative Sonogashira cross-coupling reaction of 2-ethynylaniline with ( E )-trimethyl(3, 3, 3-trifluoroprop-1-enyl)silane led to a dramatic increase in the reactivity to afford the corresponding 1, 3-enynes bearing a trifluoromethyl group on their terminal sp 2 carbon. The subsequent cyclization of these 1, 3-enynes under palladium catalysis provides access to the corresponding indoles bearing a 3, 3, 3-trifluoroprop-1-enyl group at their 2-position.