Gold(I)-Catalyzed Intermolecular Addition of Phenols and Carboxylic Acids to Olefins

Abstract

Ph3PAuOTf can catalyze efficient intermolecular addition of phenols and carboxylic acids to olefins under relatively mild conditions.

The Condensation of Carbonyl Compounds with Electron-Rich Arenes: Mercury, Thallium, Gold or a Proton?

“…With 1 mol % of AuCl 3 and three equivalents of 5 a highly selective reaction to 17 was observed, the 1 H NMR spectra taken during the reaction indicated that first in a very fast step the hydroarylation product 16 is formed, which subsequently reacts with two more molecules of 5 as indicated for the other aldehydes 11 and 13. The absence of 18 and the survival of the double bond in 14 are in accord with the observation that unactivated alkenes in gold-catalyzed reactions react at higher temperatures in non-coordinating solvents only; [20] if 5 would react with the aldehyde group of 15 first, it should be possible to isolate or at least observe 18.…”

Gold catalysis in organic synthesis: efficient intramolecular cyclization of γ-acetylenic carboxylic acids to 5-exo-alkylidene-butyrolactones

“…The versatility of AuCl was then evaluated for other functionalized acid derivatives ( Table 2). The presence of allylic or propargylic side chains was compatible with the reaction conditions and no other competitive addition to these unsaturated moieties 7 was observed ( Table 2, entries 1, 2). The chloro-or free alcohol-substituted carboxylic acids 3e-f underwent a clean and selective cyclization reaction leading to γ-lactones 6e-f in 85-95% isolated yields.…”

“…Gold(I) was chosen for its easy handling ability and its lower sensitivity to moisture. The use of toluene, dichloromethane, or 1,2-dichloroethane led to the formation of the desired lactone in lower isolated yields (Table 1, entries [6][7][8]. The versatility of AuCl was then evaluated for other functionalized acid derivatives ( Table 2).…”

Highly Chemo- and Regioselective Reaction of Hydroxybenzenes in Acidic Ionic Liquid

“…[1][2][3][4][5][6][7][8][9] There are a few examples about the selectivity tuning for the reaction of hydroxybenzenes with α,β-unsaturated compounds, however, these precedents did not give satisfactory results. Rudolf Aumann discovered that both oxa-Michael adduct and Friedel-Crafts alkylated product were produced from the reaction of 9-phenanthrol, while the reaction of phenol only afforded the oxa-Michael adduct.…”