63860-10-6Relevant articles and documents
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.
Nickel-catalyzed heck-type alkenylation of secondary and tertiary α-carbonyl alkyl bromides
Liu, Chao,Tang, Shan,Liu, Dong,Yuan, Jiwen,Zheng, Liwei,Meng, Lingkui,Lei, Aiwen
supporting information; experimental part, p. 3638 - 3641 (2012/05/20)
Ni made it! A novel Heck-type reaction of secondary and tertiary α-carbonyl alkyl bromides, most likely involving a radical process, was achieved through the use of a nickel catalyst. Various substituted styrenes and 1,1-diaryl alkenes were utilized as substrates to easily construct α-alkenyl carbonyl compounds with tertiary or quaternary carbon centers. A catalytic cycle involving NiI/NiII is proposed based on our experimental results. EWG=electron-withdrawing group.