134273-12-4Relevant articles and documents
Efficient coupling reactions of arylalkynes and aldehydes leading to the synthesis of enones
Xu, Li-Wen,Li, Lyi,Xia, Chun-Gu,Zhao, Pei-Qing
, p. 3080 - 3084 (2004)
Ionic liquids such as 1-butyl-3-methyl-1H-imidazolium 4- methylbenzenesulfonate (BmimOTs) and its 1-ethyl analogue EmimOTs are novel effective and recyclable media for acid-catalyzed coupling reaction, of aromatic alkynes with aldehydes affording (E)-enones (Scheme 1, Table) with simple recovery and easy workup due to the absence of volatile organic solvents. This transformation avoids the use of moisture-sensitive and heavy-metal Lewis acids.
Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions
Yang, Zhiyuan,Gong, Pei-Xue,Chen, Junjie,Zhang, Jie,Gong, Xu,Han, Wei
supporting information, p. 1207 - 1212 (2021/06/18)
A ligand-free palladium-catalyzed carbonylation of vinyl iodides with arylboronic acids, permitting the synthesis of chalcones and α-branched enones, has been established. This reaction proceeds smoothly at ambient pressure and temperature, and works well even with a substoichiometric amount of base. Importantly, this mild, efficient, and operationally simple protocol is suitable for the late-stage functionalization of an epiandrosterone-derived complex molecule.
Remote Functionalization of α,β-Unsaturated Carbonyls by Multimetallic Sequential Catalysis
Romano, Ciro,Fiorito, Daniele,Mazet, Clément
, p. 16983 - 16990 (2019/10/28)
The remote functionalization of α,β-unsaturated carbonyls by an array of multimetallic sequential catalytic systems is described. The reactions are triggered by hydrometalation using [Pd-H] or [Ru-H] isomerization catalysts and driven by the formation of thermodynamically more stable 1,2-vinyl arenes. The Pd-catalyzed deconjugative isomerization was combined with a Cu-catalyzed β-borylation of the transiently generated styrenyl derivatives to deliver a range of products that would not be accessible with the use of a single catalyst. [Pd/Cu] catalytic systems were also identified for the highly enantioselective α-hydroboration and α-hydroamination of the styrenyl intermediates. Difunctionalization simultaneously at the benzylic and homobenzylic positions was achieved by combining the isomerization process with Sharpless asymmetric dihydroxylation (SAD) using [Pd/Os] or [Ru/Os] couples. Starting from a simple α,β-unsaturated ester, an isomerization/dihydroxylation/lactonization sequence gave access to a naturally occurring γ-butyrolactone in good yield, with excellent diastereo- and enantioselectivity.
