Gold-Catalyzed Carbazolation Reactions of Alkynes

Abstract

Herein, we report on a Au(I)-catalyzed reaction of alkynes with carbazoles that enables a one-step synthesis of vinyl carbazoles that are important molecules for applications as photoluminescent materials. This reaction proceeds under mild conditions at room temperature, without the need of external bases, and can be employed to a variety of aromatic and aliphatic alkynes in monohydroamination and poly-hydroamination reactions. We conclude with photophysical studies of the vinyl carbazole products, which feature distinct fluorescence properties.

Bidentate Lewis Acids Derived from o‐Diethynylbenzene with Group 13 and 14 Functions

“…1,2-Diethynylbenzene (1), the organic backbone for all poly-Lewis acids discussed in this work, was synthesised according to protocols that had previously been reported. [21] 2.1. Hydrosilylation with HSiClMe 2 , HSiCl 2 Me, HSiCl 3…”

“…The synthesis of precursor 1 was described previously. [21] Chlorodimethylsilane, dichloromethylsilane and trichlorosilane were purchased from Sigma‐Aldrich and used without further purification. Karstedt's catalyst was purchased from ABCR (3–3.5 % Pt).…”

Synthesis of Bifunctional Boron‐Lewis Acids – Thorough Investigation of the Adduct Formation with Pyrimidine

“…General : 1,2‐Diethynylbenzene, [31] perchlorobenzo[ d ][1,3,2]dioxaborole, [32] 2‐chlorobenzo[ d ][1,3,2]dioxaborole [33] and chlorobis(3,5‐dimethylphenyl)borane [34] were synthesized according to literature protocols. Pyrimidine was dried over potassium hydroxide and used after distillation.…”

Physical and photophysical properties of a linear copper(I) complex of a bulky acenapthene-based NHC ligand

“…The three compounds 1H.Cl, 2 and 3 all show a strong absorption band at 233-235 nm with e = 23-27 × 10 3 M -1 cm -1 and another between 279-292 nm with e = 18-24 × 10 3 M -1 cm -1 ; both of which are characteristic of locally-excited transitions on the NHC, as predicted by TD-DFT (Table 4). Carbazole has a characteristic absorption spectrum with peaks at 266 and 290 nm; [42] however, these are largely obscured in the absorption spectrum of 3, with only a peak attributed to a LC transition on carbazole observed as a shoulder at 310 nm. The transitions observed at 326 and 375 nm can both be assigned to predominantly ligand-to-ligand charge transfer ( 1 LLCT) transition from Cz to IPrBIAN (HOMO-5→LUMO and HOMO→LUMO+1, respectively).…”