Palladium‐Catalyzed Selective Synthesis of Naphthalenes and Indenones and Their Luminescent Properties

Abstract

Selective synthesis of functionalized naphthalenes and indenones by palladium-catalyzed cyclization of o-haloacetophenones and terminal alkynes in the presence of a secondary amine is reported. Under a nitrogen atmosphere, the palladium-catalyzed reaction of o-haloacetophenones with terminal alkynes in the presence of wet secondary amines generated 1-(dialkylamino)-3-aryl/alkylnaphthalenes. When

Isoquinolino[4,3,2-de]phenanthridine: synthesis and its use in 1,3-dipolar cycloadditions to form nitrogen-containing polyaromatic hydrocarbons

“…The C-N bond lengths and C1-N1-C4 angles in these pyrrole structures are consistent with those of previously reported fused 1,2,3,4,5pentaarylpyrroles. 11,14 Azomethine ylide 1 was found to react with electrondeficient alkenes. The reaction with methyl acrylate produced pyrrolidine 6d in 61% yield as an inseparable mixture of endo and exo adducts (ca.…”

“…8,9 The method presented is highly effective for the synthesis of fused 1,2,3,4,5-pentaarylpyrroles via reactions with diarylacetylenes. To the best of our knowledge, only few compounds with a fused 1,2,3,4,5-pentaarylpyrrole structure, such as 2,3-diaryl fused pyrroles (dibenzo[e,g]indole 10 and diacenaphtho[1,2-b:1',2'-d]pyrrole 11 ), 3,4-diaryl fused pyrroles (dibenzo[e,g]isoindole 12,13 and acenaphtho[1,2-c]pyrrole 14 ), and pyrrole-fused azacorronenes, 5b have been reported. Scheme 1 illustrates the synthesis of isoquinolino[4,3,2de]phenanthridine (1) starting from 2,6-dibromo-4-tertbutylaniline (2).…”

Controllable Multicolor Upconversion Luminescence by Tuning the NaF Dosage

“…One‐pot strategies for the synthesis of various useful cyclic compounds based on the Cu‐catalyzed α‐arylation of activated ketones have been investigated, but rarely applied to simple methyl ketones 5,6. Herein, we would like to report a facile construction of 1‐naphthols via cyclization from ortho ‐iodoacetophenones7 and methyl ketones catalyzed by CuI. The reaction was realized under mild conditions initiated by a rare Cu‐catalyzed arylation of simple methyl ketones (Scheme ).…”

Exploiting the Versatility of Palladium Catalysis: A Modern Toolbox for Cascade Reactions

“…Wang et al developed the synthesis of aminonaphthalene derivatives 97 in 15-98 % yield from o-haloacetophenone 96 and terminal alkynes with moist secondary amine (Scheme 13). [26] Sonogashira coupling of enamine 96 a with alkyne followed by intramolecular nucleopalladation afforded vinylÀ Pd species 96 c, which provided the protonation product 97. A similar cyclization followed by metal-assisted Losson rearrangement was reported for substituted 1-naphthyl amines 100 in good yields (68-94 %) (Scheme 13).…”