894-15-5Relevant academic research and scientific papers
Cobalt-catalyzed annulation of styrenes with α-bromoacetic acids
Nguyen, Tung T.,Ngo, Bao H. T.,Le, Huy X.,Vu, Linh N. P.,To, Tuong A.,Phan, Anh N. Q.,Phan, Nam T. S.
, p. 5451 - 5455 (2021/02/12)
We report a method for addition of α-bromophenylacetic acids to vinyl C-C bonds in styrenes to afford γ-lactones. Reactions employed a simple cobalt catalyst Co(NO3)2·6H2O in the presence of dipivaloylmethane (dpm) ligand.
Organo-photoredox-catalyzed atom-transfer radical substitution of alkenes with α-carbonyl alkyl halides
Nishikata, Takashi,Hirata, Goki,Shimada, Taisei
supporting information, p. 8952 - 8956 (2020/12/02)
A light-driven atom-transfer radical substitution (ATRS) and carboesterification reaction of alkenes with alkyl halides has been developed using PTH as the organo-photoredox catalyst. Two types of products were obtained, depending on the additive and solvent used during the reaction. Primary, secondary, and tertiary alkyl halides reacted to give the ATRS products. This protocol has several advantages: it requires mild reaction conditions and a low catalyst loading and exhibits a broad substrate scope and good functional group tolerance. Mechanistic studies indicate that alkyl radicals might be generated as the key intermediates via photocatalysis, providing a new direction for ATRS reactions.
Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives
Iwasaki, Masayuki,Miki, Natsumi,Ikemoto, Yuichi,Ura, Yasuyuki,Nishihara, Yasushi
supporting information, p. 3848 - 3852 (2018/07/25)
An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.
A novel intermolecular synthesis of γ-lactones via visible-light photoredox catalysis
Wei, Xiao-Jing,Yang, Deng-Tao,Wang, Lin,Song, Tao,Wu, Li-Zhu,Liu, Qiang
supporting information, p. 6054 - 6057 (2014/01/06)
Direct γ-lactone formation via visible-light photoredox catalysis has been achieved efficiently including hydroxylalkylation of aromatic alkenes and transesterification. The present photocatalytic protocol has good regioselectivity and substrate compatibility, affording a novel way to intermolecular γ-lactone synthesis by the reaction of styrenes with α-bromo esters in the absence of any external oxidants.
