13305-44-7Relevant academic research and scientific papers
Coupling Reaction between Aldehydes and Non-Activated Hydrocarbons via the Reductive Radical-Polar Crossover Pathway
Yahata, Kenzo,Sakurai, Shu,Hori, Shuhei,Yoshioka, Shin,Kaneko, Yuki,Hasegawa, Kai,Akai, Shuji
supporting information, p. 1199 - 1203 (2020/02/04)
Herein, we describe the generation of an organochromium-type carbanion species from a non-activated C-H bond and its nucleophilic addition to aldehydes. The catalytic carbanion generation occurred through formal deprotonation of a non-activated C-H bond under mild conditions and did not need the prefunctionalization or anion stabilizing group. Carbon radical intermediates generated by decatungstate photocatalyst-mediated hydrogen abstraction were captured by a chromium salt with the reductive radical-polar crossover reaction to produce organochromium carbanions.
A new method for alkylation of aromatic aldehydes using alkylboron chloride derivatives in the presence of oxygen
Kabalka, George W,Wu, Zhongzhi,Ju, Yuhong
, p. 3243 - 3248 (2007/10/03)
Reactions of aromatic aldehydes with alkylboron chloride derivatives in the presence of oxygen have been investigated. Dialkylboron chlorides react with aryl aldehydes to produce arylalkylmethanols in good to excellent yields. Under the same reaction conditions, alkylboron dichlorides lead to the formation of arylalkyl chlorides.
Alkylation of aromatic aldehydes with alkylboron chloride derivatives
Kabalka, George W,Wu, Zhongzhi,Ju, Yuhong
, p. 1663 - 1670 (2007/10/03)
The reaction of aryl aldehydes with alkylboron chlorides has been investigated. Monoalkylboron dichlorides react with aryl aldehydes in hexane under reflux conditions to give a mixture of dichloroarylmethane and benzyl chloride. Under the same reaction conditions, dialkylboron chlorides lead to formation of a mixture of benzyl chloride and the chloroalkylation product. In the presence of a base such as 2,6-lutidine, the reactions of monoalkylboron dichlorides with aryl aldehydes yield small amounts of the desired alkylation products at room temperature. Dialkylboron chlorides react with aryl aldehydes in hexane in the presence of base to generate the corresponding arylalkylmethanols in good yields.
Unconjugated Arylcyclopropanes. Acid-Catalyzed Addition of Acetic Acid to Highly Hindered Arylcyclopropanes
Creary, Xavier
, p. 4653 - 4659 (2007/10/02)
The adduct of 1-naphthylcarbene and norbornene, endo-3-(1-naphthyl)-exo-tricyclo2,4>octane (9) has been prepared. 1H and 13C NMR spectra of this system indicate that the unconjugated arylcyclopropane conformation is favored.Rotation about the naphthyl-cyclopropane bond is restricted.The temperature-dependent NMR indicates a 16.9 kcal/mol barrier to attainment of the conjugated conformation.Acetic acid adds readily under acid catalysis to the phenyl analogue exo-3-phenyl-exo-tricyclo2,4>octane (3) and more slowly to the more strained endo-3-phenyl-exo-tricyclo2,4>octane (4).Kinetic data suggest the involvement of a cationic intermediate with little transition-state charge development at the benzylic carbon.The rates of addition to substituted analogues of 3 and 4 correlate with Hammett ? values, giving ρ values of 2.53 and 2.35, respectively.Product-analysis data support the involvement of a benzylic cation, 23.The slower rate of reaction of the more strained endo isomers has been interpreted in terms of a barrier to attainment of the conjugated conformation which appears to be the favorable conformation for protonation of arylcyclopropanes.This suggestion is supported by the observation that the unconjugated systems, exo- and endo-3-(2,6-dimethylphenyl)-exo-tricyclo-2,4>octanes (27 and 28), add acetic acid 480 and 6.2 x 104 times, respectively, more slowly than 3.
