Borane-catalyzed indole synthesis through intramolecular hydroamination. Issue 5 (16th January 2017)

• Record Type: Journal Article
• Authors: Tussing, Sebastian; Ohland, Miriam; Wicker, Garrit; Flörke, Ulrich; Paradies, Jan
• Is Part Of: Dalton transactions. Volume 46:Issue 5(2017)
• Page Start: 1539
• Page End: 1545
• Publication Date: 2017-01-16
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c6dt04725d
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : Catalytic metal-free intramolecular hydroamination for the synthesis of indoles and tetrahydroisoquinolines was achieved. Abstract : The reaction of 2-alkynyl anilines with catalytic amounts of B(C6 F5 )3 (5 mol%) resulted in the formation of 2-substituted indoles according to an intramolecular hydroamination in good to excellent yields. Reaction intermediates as well as products were characterized by NMR spectroscopy and by X-ray crystallography. The domino hydroamination/hydrogenation sequence allowed the efficient synthesis of tetrahydroquinoline8 in good yield.