Synthesis and Catalytic Activity of Coumarin‐ and Chrysin‐Tethered Triazolylidene Gold(I) Complexes

• Published in: European journal of inorganic chemistry Vol. 2018; no. 42; pp. 4622 - 4629
• Main Authors: Ruiz‐Mendoza, Francisco J., Mendoza‐Espinosa, Daniel, González‐Montiel, Simplicio
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 15.11.2018; Wiley Subscription Services, Inc
• Subjects: Alkylation; Alkynes; Catalysis; Catalytic activity; Chemical synthesis; Chemistry; Chemistry, Inorganic & Nuclear; Chrysin; Coumarin; Cycloaddition; Gold; Infrared spectroscopy; Inorganic chemistry; Mesoionic carbenes; NMR spectroscopy; Physical Sciences; Science & Technology; Triazolium salts; X ray spectra; X-ray diffraction; Gold; Triazolium salts; PINCER LIGAND; TRANSITION-METAL-COMPLEXES; SILVER(I) COMPLEXES; ANTICANCER AGENTS; TERMINAL ALKYNES; N-HETEROCYCLIC CARBENES; Mesoionic carbenes; Coumarin; PALLADIUM(II) COMPLEXES; Chrysin; BIOLOGICAL EVALUATION; RING-OPENING POLYMERIZATION
• ISSN: 1434-1948; 1099-0682
• DOI: 10.1002/ejic.201800921

A series sterically‐encumbered coumarin‐ (1) and chrysin‐functionalized triazolium salts (2,3) have been synthesized stepwise via copper catalyzed alkyne–azide cycloaddition and N‐alkylation procedures. Their one‐pot deprotonation with KHMDS in presence of AuCl(SMe2) allowed for the preparation of the corresponding triazolylidene gold(I) complexes (4–6) in high yields (75–92 %). All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, FT‐IR, elemental analyses and in the case of triazole F, triazolium 1 and the gold complex 4, by single‐crystal X‐ray diffraction. The new triazolylidene gold complexes (4–6) were tested as precatalysts in the synthesis of indole derivatives via an intramolecular hydroamination reaction of several readily available anilines. We report the synthesis and characterization a series of coumarin‐ and chrysin‐functionalized triazolylidene gold(I) complexes. Their catalytic performance in the synthesis of indoles via an intramolecular hydroamination reaction of several anilines is discussed.