27751-80-0Relevant articles and documents
Visible-Light-Driven, Metal-Free Divergent Difunctionalization of Alkenes Using Alkyl Formates
Zheng, Ming,Hou, Jing,Zhan, Le-Wu,Huang, Yan,Chen, Ling,Hua, Li-Li,Li, Yan,Tang, Wan-Ying,Li, Bin-Dong
, p. 542 - 553 (2021/01/14)
In recent decades, difunctionalization of alkenes has received considerable attention as an efficient and straightforward way to increase molecular complexity. However, examples of the difunctionalization of alkenes initiated by the intermolecular addition of alkoxycarbonyl radicals providing substituted alkanoates are still rare. Herein, we present the visible light-driven metal-free divergent difunctionalization of alkenes triggered by the intermolecular addition of alkoxycarbonyl radicals under ambient conditions. Employing alkyl formates as precursors of alkoxycarbonyl radicals and 4CzIPN as the photocatalyst, a variety of substituted alkanoates, including β-alkoxy, β-hydroxy, β-dimethoxymethoxy, and β-formyloxy alkanoates, could be facilely accessed with high functional group tolerance and high efficiency. Moreover, the mechanism study revealed that β-hydroxy alkanoates were generated by a selective decomposition of orthoformates promoted by the N-alkoxyazinium salt.
A tandem enol silane formation-Mukaiyama aldol reaction mediated by TMSOTf
Downey, C. Wade,Johnson, Miles W.
, p. 3559 - 3562 (2007/10/03)
A slight excess of silyl trifluoromethanesulfonate mediates a tandem enol silane formation-Mukaiyama aldol reaction in the presence of Hunig's base. Preformation of the enol silane is unnecessary for efficient reactions, which proceed in 75-97% yield for the addition of aryl methyl ketones and acetate esters to non-enolizable aldehydes. Mechanistic data suggests that free amine is crucial for full conversion.
A general method for the formation of zinc enolate equivalents from iodoacetates by diisopropylzinc-iodine exchange reaction: Preparation of β-Hydroxy esters
Sato,Takizawa,Soai
, p. 2825 - 2826 (2007/10/03)
Diisopropylzinc is found to be a highly efficient reagent for the formation of zinc enolate equivalents from various iodoacetates via iodine-Zinc exchange reaction at room temperature, affording β-Hydroxy esters in high yields by the reaction with aldehydes and ketones.