24241-74-5Relevant articles and documents
Expanding the Scope of Photocatalysis: Atom Transfer Radical Addition of Bromoacetonitrile to Aliphatic Olefins
Voutyritsa, Errika,Triandafillidi, Ierasia,Kokotos, Christoforos G.
, p. 2466 - 2470 (2018)
An efficient photocatalyzed bromocyanomethylation of alkenes is reported. Among a range of organocatalysts and metal complexes, Ir(ppy)3 proved to be the best photocatalyst in promoting the addition of BrCH2CN to olefins. This photocatalytic atom transfer protocol can be expanded into a wide substrate scope of aliphatic olefins bearing various functional groups, leading to the corresponding products in good to excellent yields. In addition, linchpin catalysis was developed, since the bromo group can undergo further transformation into useful functional groups, such as the synthesis of amino acids.
Radical-polar crossover reactions of vinylboron ate complexes
Kischkewitz, Marvin,Okamoto, Kazuhiro,Mück-Lichtenfeld, Christian,Studer, Armido
, p. 936 - 938 (2017/03/15)
Vinyl boronic esters are valuable substrates for Suzuki-Miyaura cross-coupling reactions. However, boron-substituted alkenes have drawn little attention as radical acceptors, and the radical chemistry of vinylboron ate complexes is underexplored. We show here that carbon radicals add efficiently to vinylboron ate complexes and that their adduct radical anions undergo radical-polar crossover: A 1,2-alkyl/aryl shift from boron to the α-carbon sp2 center provides secondary or tertiary alkyl boronic esters. In contrast to the Suzuki-Miyaura coupling, a transition metal is not required, and two carbon-carbon bonds are formed. The valuable boronic ester moiety remains in the product and can be used in follow-up chemistry, enlarging the chemical space of the method. The cascade uses commercial starting materials and provides access to perfluoroalkylated alcohols, γ-lactones, γ-hydroxy alkylnitriles, and compounds bearing quaternary carbon centers.
Ene-carbonyl reductive coupling mediated by zinc and ammonia for the synthesis of γ-hydroxybutyric acid derivatives
Yeh, Chien-Hung,Korivi, Rajendra Prasad,Cheng, Chien-Hong
supporting information, p. 1338 - 1344 (2013/06/27)
The reductive coupling of an aryl carbonyl group with an activated alkene to give the corresponding γ-hydroxybutyric acid (GHBA) derivative was achieved in the presence of zinc and ammonia. A board scope of GHBA derivatives could be synthesized under ambient conditions by this method. A mechanism involving a Zn-ketyl radical as the key intermediate is proposed. Copyright
