116076-79-0Relevant academic research and scientific papers
Metal-free oxidative C(sp3)-H bond functionalization of alkanes and alkylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols
Zhao, Jincan,Fang, Hong,Song, Ruichun,Zhou, Jie,Han, Jianlin,Pan, Yi
, p. 599 - 602 (2014)
An oxidative C(sp3)-H bond functionalization of alkanes and alkylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols using di-tert-butyl peroxide (DTBP) as the oxidant was established, which tolerates a wide range of simpl
NNN pincer Ru(II)-complex-catalyzed α-alkylation of ketones with alcohols
Cao, Xiao-Niu,Wan, Xiao-Min,Yang, Fa-Liu,Li, Ke,Hao, Xin-Qi,Shao, Tian,Zhu, Xinju,Song, Mao-Ping
, p. 3657 - 3668 (2018/04/14)
A series of novel ruthenium(II) complexes supported by a symmetrical NNN ligand were prepared and fully characterized. These complexes exhibited good performance in transfer hydrogenation to form new C-C bonds using alcohols as the alkylating agents, generating water as the only byproduct. A broad range of substrates, including (hetero)aryl- or alkyl-ketones and alcohols, were well tolerated under the optimized conditions. Notably, α-substituted methylene ketones were also investigated, which afforded α-branched steric hindrance products. A potential application of α-alkylation of methylene acetone to synthesize donepezil was demonstrated, which provided the desired product in 83% yield. Finally, this catalytic system could be applied to a one-pot double alkylation procedure with sequential addition of two different alcohols. The current protocol is featured with several characteristics, including a broad substrate scope, low catalyst (0.50 mol %) loadings, and environmental benignity.
Radical 1,2-Alkylarylation/Acylarylation of Allylic Alcohols with Aldehydes via Neophyl Rearrangement
Pan, Changduo,Ni, Qingting,Fu, Yu,Yu, Jin-Tao
, p. 7683 - 7688 (2017/07/26)
A metal-free 1,2-alkylarylation of allylic alcohols with aliphatic aldehydes through concomitant radical neophyl rearrangement was developed, providing 1,2-diphenyl-3-alkyl propanones in moderate to good yields. Moreover, when cyclopropanecarbaldehyde and aryl carbaldehydes were concerned, acylarylation was involved leading to 1,4-dicarbonyl compounds.
Polar Effects in Radical Addition Reactions: Borderline Cases
Giese, Bernd,He, Jianing,Mehl, Wolf
, p. 2063 - 2066 (2007/10/02)
Methyl radicals substituted by one ester or nitrile group are on the borderline between nucleophilic and electrophilic behavior.In addition reactions of these borderline radicals to styrenes, polar effects of both, electron-withdrawing and electron-donating substituents at the alkene, increase the rates.But these polar effects are smaller compared to those of nucleophilic or electrophilic radicals.In consequence, the stability of the radicals formed during the addition of the borderline radicals to styrenes are of major importance for the rate of the reaction.
