Chemoselective reductive alkynylation of tertiary amides by Ir and Cu() bis-metal sequential catalysis

• Published in: Chemical communications (Cambridge, England) Vol. 52; no. 8; pp. 11967 - 1197
• Main Authors: Huang, Pei-Qiang, Ou, Wei, Han, Feng
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 29.09.2016
• Subjects: Aldehydes; Alkynes; Amides; Amines; Catalysis; catalytic activity; chemical reactions; Chemistry; Chemistry, Multidisciplinary; chemoselectivity; copper; Coupling; Direct reduction; Functional groups; iridium; moieties; Physical Sciences; Science & Technology; ORGANOMETALLIC REAGENTS; HIGHLY ENANTIOSELECTIVE CONSTRUCTION; SECONDARY AMIDES; DIRECT TRANSFORMATION; TERMINAL ALKYNES; MAGNESIUM REAGENTS; NUCLEOPHILIC-ADDITION; C-H ACTIVATION; GRIGNARD-REAGENTS; LITHIUM ACETYLIDES
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/c6cc05318a

We report herein a convenient and versatile method for the direct reductive alkynylation of tertiary amides to give propargylic amines through sequential Ir-catalysed hydrosilylation-Cu( i )-catalysed alkynylation. The reactions proceed chemoselectively at the amide group in the presence of several sensitive functional groups including the very reactive aldehyde group on either the amide or the alkyne coupling partner. The method is general for tert -amides with or without α-hydrogen. We report a versatile method for the direct, catalytic reductive alkynylation of tertiary amides to give propargylic amines.