74600-36-5Relevant academic research and scientific papers
Photoredox-Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C?H Bond Activation
Guo, Kai,Huang, Jun,Li, Anding,Li, Yuanhe,Yang, Zhen,Zhang, Zhongchao
supporting information, p. 11660 - 11668 (2020/05/25)
Photoredox-catalyzed isomerization of γ-carbonyl-substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time by C?H bond activation. This catalytic redox-neutral process resulted in the synthesis of 1,4-dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transformed into their corresponding carbonyl compounds. Density functional theory calculations show that the carbonyl group at the γ-position of allylic alcohols are beneficial to the formation of their corresponding allylic alcohol radicals with high vertical electron affinity, which contributes to the completion of the photoredox catalytic cycle.
PREPARATION AND REACTIVITY OF FUNCIONALIZED ALKENYL-ZINC, -COPPER, AND -CHROMIUM ORGANOMETALLICS
Knochel, Paul,Rao, C. Janakiram
, p. 29 - 48 (2007/10/02)
β-Halogeno-α,β-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45 deg C, 1-4h).These funcionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97percent yield.The addition of a THF solution of CuCN*2LiCl to 2a affords the corresponding organocopper derivatives 2b which rect with electophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfuncional unsaturated carbonyl compounds in 71-95percent yield.The insertion of chromium (II) chloride to β-iodo and to some β-(p-tosyl)enones in DMF furnishes new funcionalized chromium (III) organometallics 2c which react with aldehydes providing γ-hydroxy unsaturated carbonyl derivatives in 40-91percent yield.The synthetic scope and the limitations of this methodology are discussed. Key words: funcionalized organozinc halides, alkenylchromium(III) compounds, copper-zinc organometallics.
An efficient and versatile synthesis of β-alkylidene-α,α-disubstituted cyclopentanones
Burke, Steven D.,Shearouse, Sandra A.,Burch, Daniel J.,Sutton, Randy W.
, p. 1285 - 1288 (2007/10/02)
A direct, two step synthesis of specifically-substituted cyclopentanones utilizing α-alkoxy organolithium reagents is reported.
