Refernces
10.1039/C9OB00587K
The research investigates a gold(I)-catalysed method for the intermolecular hydroamination of internal alkynes to synthesize functionalized vinylazoles under solvent-free conditions. The purpose is to develop an efficient and selective route to produce N-functionalized azoles, which are important scaffolds in pharmaceuticals and bioactive compounds. The study uses gold(I) catalysts such as [Au(IPr)(OH)], [Au(IPr)][NTf2], and [{Au(IPr)}2(μ-OH)][BF4], along with internal alkynes like diphenylacetylene and various azole nucleophiles including benzotriazole and triazoles. The reactions were optimized using additives like NBu4OTf and performed under thermal or microwave heating. The results showed high regio-, chemo-, and stereoselectivity, yielding (Z)-enamines with good to high yields. The subsequent hydrogenation of these enamines led to the formation of saturated azoles in good yields. The study concludes that this gold(I)-catalysed method offers a practical, scalable, and atom-economical alternative for synthesizing a wide range of functionalized azoles.
10.1021/ic800314p
The study focuses on the synthesis, structural characterization, and anti-inflammatory activity of a series of gold(I) complexes of the type [(AuPEt3)2xspa], where H2xspa represents various 3-(aryl)-2-sulfanylpropenoic acids. The chemicals involved include AuPEt3Cl (triethylphosphinegold(I) chloride) as the gold source, and various 3-(aryl)-2-sulfanylpropenoic acids (H2xspa) as ligands. The acids used include H2pspa (3-phenyl), H2Clpspa (3-(2-chlorophenyl)-), H2-o-mpspa (3-(2-methoxyphenyl)-), H2-p-mpspa (3-(4-methoxyphenyl)-), H2-o-hpspa (3-(2-hydroxyphenyl)-), H2-p-hpspa (3-(4-hydroxyphenyl)-), H2diBr-o-hpspa (3-(3,5-dibromo-2-hydroxyphenyl)-), H2fspa (3-(2-furyl)-), H2tspa (3-(2-thienyl)-), and H2-o-pyspa (3-(2-pyridyl)). The role of these chemicals is to form gold(I) complexes that are then characterized by spectroscopic methods (IR, 1H, 13C, and 31P NMR), mass spectrometry, and X-ray diffractometry. The study also investigates the anti-inflammatory activity of these complexes against plantar edema induced by carrageenan in rats, revealing that most of the complexes exhibit significant anti-inflammatory effects, with the o-hpspa and tspa derivatives showing particularly high activity.
10.1016/j.tet.2008.10.109
The research focuses on the development of novel gold(I)-catalyzed cascade cycloisomerization processes for the synthesis of multisubstituted 1,3-dienes and naphthalenes. The purpose of this study was to create a domino process involving a tandem sequence of 1,3- and 1,2-migrations of two different migrating groups, leading to the formation of naphthalene skeletons. The conclusions drawn from the research demonstrate that β-unsubstituted propargylic phosphates, acetates, and pivalates can undergo a mild and stereoselective gold(I)-catalyzed isomerization, resulting in the corresponding 1-oxy-1,3-diene esters. Additionally, a variety of densely substituted naphthalenes can be synthesized through a cascade cycloisomerization process. The chemicals used in these processes include propargylic esters, gold(I) catalysts such as Ph3PAuCl/AgOTf, and various substituents like methoxy, trifluoromethyl, and furyl groups. The study provides a new and efficient method for assembling naphthalenes, which were not accessible through existing methodologies.
10.1021/ol800219k
The research focuses on the gold(I)-catalyzed rearrangement of (3-acyloxyprop-1-ynyl)oxiranes, a novel and mild method for the synthesis of acyloxylated divinyl ketones. The study explores the alkynophilic and oxophilic properties of gold salts or complexes, which are known to facilitate unique chemical transformations. The researchers hypothesized that these properties could be combined to create new chemistry, and they designed experiments to test this hypothesis using R- and α-alkynyl epoxides. The study concluded that this gold-catalyzed rearrangement is an original and efficient approach to synthesize functionalized divinyl ketones under mild conditions, and it provides a foundation for further exploration of gold catalysts in organic synthesis.
