6048-82-4Relevant articles and documents
Synthesis of α-Alkylated Ketones via Selective Epoxide Opening/Alkylation Reactions with Primary Alcohols
Gen?, Serta?,Gülcemal, Süleyman,Günnaz, Salih,?etinkaya, Bekir,Gülcemal, Derya
supporting information, p. 5229 - 5234 (2021/07/19)
A new method for converting terminal epoxides and primary alcohols into α-alkylated ketones under borrowing hydrogen conditions is reported. The procedure involves a one-pot epoxide ring opening and alkylation via primary alcohols in the presence of an N-heterocyclic carbene iridium(I) catalyst, under aerobic conditions, with water as the side product.
Unveiling the catalytic nature of palladium-N-heterocyclic carbene catalysts in the α-alkylation of ketones with primary alcohols
?etinkaya, Bekir,Ero?lu, Zafer,Gülcemal, Süleyman,Metin, ?nder,Ovezova, Mamajan
supporting information, p. 10896 - 10908 (2021/08/17)
We report herein the synthesis of four new Pd-PEPPSI complexes with backbone-modified N-heterocyclic carbene (NHC) ligands and their application as catalysts in the α-alkylation of ketones with primary alcohols using a borrowing hydrogen process and tandem Suzuki-Miyaura coupling/α-alkylation reactions. Among the synthesized Pd-PEPPSI complexes, complex2chaving 4-methoxyphenyl groups at the 4,5-positions and 4-methoxybenzyl substituents on the N-atoms of imidazole exhibited the highest catalytic activity in the α-alkylation of ketones with primary alcohols (18 examples) with yields reaching up to 95%. Additionally, complex2cwas demonstrated to be an effective catalyst for the tandem Suzuki-Miyaura-coupling/α-alkylation of ketones to give biaryl ketones with high yields. The heterogeneous nature of the present catalytic system was verified by mercury poisoning and hot filtration experiments. Moreover, the formation of NHC-stabilized Pd(0) nanoparticles during the α-alkylation reactions was identified by advanced analytical techniques.
Rhodium-Catalyzed Remote Isomerization of Alkenyl Alcohols to Ketones
Dong, Wenke,Yang, Hongxuan,Yang, Wen,Zhao, Wanxiang
supporting information, (2020/02/28)
We develop herein an efficient rhodium-catalyzed remote isomerization of aromatic and aliphatic alkenyl alcohols into ketones. This catalytic process, with a commercially available catalyst and ligand ([RhCl(cod)]2 and Xantphos), features high efficiency, low catalyst loading, good functional group tolerance, a broad substrate scope, and no (sub)stoichiometric additive. Preliminary mechanistic studies suggest that this transformation involves an iterative dissociative β-hydride elimination-migration insertion process.
