32499-31-3Relevant academic research and scientific papers
Synthesizing method of alpha-arone or alpha-hetero-arone
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Paragraph 0032; 0033; 0035, (2018/09/08)
The invention discloses a synthesizing method of alpha-arone or alpha-hetero-arone and belongs to the technical field of metal organic catalyzing. The synthesizing method has the advantages that a terminal alkynyl compound, oxynitride and a proton supply agent is catalyzed by univalence metal salt to obtain N-O pyridine oxynitride enol salt, purification and separation are not needed, and the N-Opyridine oxynitride enol salt is allowed to have reaction with arene and hetero-arene in a one-pot manner to obtain the alpha-arone or alpha-hetero-arone; the method is high in functional group tolerance, wide in substrate application range, high in yield, simple and easy to operate and easy in final product separation and purification.
Regioselective Arene and Heteroarene Functionalization: N-Alkenoxypyridinium Salts as Electrophilic Alkylating Agents for the Synthesis of α-Aryl/α-Heteroaryl Ketones
Zhai, Rong L.,Xue, Yun S.,Liang, Ting,Mi, Jia J.,Xu, Zhou
supporting information, p. 10051 - 10059 (2018/07/30)
A direct regioselective functionalization of arenes and heteroarenes using N-alkenoxypyridinium salts as electrophilic alkylating agents for the synthesis of α-aryl/heteroaryl ketones has been developed. The method generates alkylating agents from alkynes and N-pyridine oxide followed by site-selective electrophilic substitution with a broad range of arenes and heteroarenes including benzene derivates, phenols, ethers, indoles, pyrroles, furans, and thiophenes in one pot. Kinetic isotope effect measurements and DFT studies reveal that this reaction likely proceeds through a carbon-cation intermediate.
Reaction of α-Silyl Esters with Grignard Reagents: A Synthesis of β-Keto Silanes and Ketones. Preparation of the Douglas Fir Tussock Moth Pheromone
Larson, Gerald L.,Hernandez, David,Lopez-Cepero, Ingrid Montes de,Torres, Luz E.
, p. 5260 - 5267 (2007/10/02)
A variety of α-diphenylmethylsilyl esters have been prepared and reacted with Grignard reagents.The reaction is relatively slow in refluxing THF and can be controlled to allow the addition of 1 equiv of the Grignard reagent, providing the corresponding β-keto silane.Protiodesilylation of the β-keto silane results in the overall conversion of an ester to a ketone.This ester to ketone methodology has been applied to a two-step synthesis of the pheromone of the Douglas fir tussock moth.The β-keto silanes are viable precursors to regioselectively generated enol silyl ethers.The reaction of ethyl 2-methyl-2-(diphenylmethylsilyl)propionate with vinylmagnesium bromide or 2-methyl 1-propenylmagnesium bromide results in the addition of 2 equiv of the Grignard reagent, the second in a Michael fashion.
Transformation of Alkyl Halides to Aldehydes Having Two Additional Carbon Atoms
Shankaran, K.,Talekar, D. G.,Rao, A. S.
, p. 408 - 410 (2007/10/02)
Methyl 3-oxo-4-phenylbutanoate (6) reacts with alkyl halides (1a-g) in the presence of NaH/benzene to furnish alkylated β-keto esters (2a-g).Hydrolysis of 2a-g gives benzyl ketones (3a-g), which on reduction with sodium borohydride give the homobenzylic alcohols (4a-g).The alcohols (4a-g) are readily fragmented to aldehydes (5a-g) on heating with lead tetraacetate/iodine.
