114222-35-4Relevant academic research and scientific papers
Metal-free, visible-light-mediated, decarboxylative alkylation of biomass-derived compounds
Schwarz, Johanna,K?nig, Burkhard
, p. 4743 - 4749 (2016)
This work describes a mild, environmentally friendly method to activate natural carboxylic acids for decarboxylative alkylation. After esterification of biomass-derived acids to N-(acyloxy)phthalimides, the active esters are cleaved reductively by photocatalysis to give alkyl radicals, which undergo C-C bond formation with electron-deficient alkenes. This reaction is catalyzed by the organic dye eosin Y and green light (535 nm) and the scope of acids includes abundant amino acids, α-oxy acids and fatty acids which are available from renewable resources.
Direct Decarboxylative-Decarbonylative Alkylation of α-Oxo Acids with Electrophilic Olefins via Visible-Light Photoredox Catalysis
Chen, Jian-Qiang,Chang, Rui,Wei, Yun-Long,Mo, Jia-Nan,Wang, Zhu-Yin,Xu, Peng-Fei
, p. 253 - 259 (2018/02/19)
The decarbonylation of primary, secondary, and tertiary alkyl-substituted acyl radicals has been investigated through photoredox catalysis. A series of quaternary carbons and γ-ketoesters have been directly constructed by the photoredox 1,4-conjugate addi
Amphiphilic Reactions by Means of Exceptionally Bulky Organoaluminum Reagents. Rational Approach for Obtaining Unusual Equatorial, Anti-Cram, and 1,4 Selectivity in Carbonyl Alkylation
Maruoka, Keiji,Itoh, Takayuki,Sakurai, Minoru,Nonoshita, Katsumasa,Yamamoto, Hisashi
, p. 3588 - 3597 (2007/10/02)
Exceptionally bulky, oxygenophilic organoaluminum reagents, methylaluminum bis(2,6-di-tert-4-alkylphenoxide) (MAD and MAT), have been successfully utilized for stereoselective activation of carbonyl moiety.Combination of MAD or MAT with carbon nucleophiles such as organolithiums or Grignard reagents generates a new amphiphilic reaction system in which the alkylation may be interpreted as the nucleophilic addition of a reactive organometallic compound to an electrophilically activated carbonyl substrate in order to account for the regio- and stereochemical consequences.In contrast to the ordinary alkylations, the amphilic alkylation disclosed herein would be categorized into the new, yet unexplored class of alkylation that exhibits high chemoselectivity to carbonyl compounds, and more significantly it allows excellent equatorial and anti-Cram selectivity in carbonyl alkylations, hitherto difficult by the existing methodologies.Further, unusual conjugate addition of organolithium reagents to α,β-unsaturated carbonyl compounds has been accomplished by using the amphiphilic reaction system.
