62509-81-3Relevant academic research and scientific papers
Visible-light-promoted α-methoxymethylation and aminomethylation of ketones with methanol as the C1 source
Yang, Jingya,Liu, Cai,Zhou, Hongyan,Fan, Rundong,Ma, Ben,Li, Zheng
supporting information, p. 5572 - 5576 (2021/07/02)
Visible-light-promoted α-methoxymethylation and aminomethylation of ketones using methanol as a sustainable C1 source have been developed. With rose bengal as the photosensitizer and air as the green oxidant, the methoxymethylation reactions proceeded smoothly under visible light irradiation at ambient temperature. Additionally, a one-pot one-step α-aminomethylation of ketones was achieved by adding N-nucleophiles. Preliminary mechanism studies suggest that the reaction mainly proceedsviaa radical pathway.
Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol
Biswal, Priyabrata,Chandrasekhar, Vadapalli,Meher, Sushanta Kumar,Samser, Shaikh,Venkatasubbaiah, Krishnan
supporting information, (2021/11/01)
One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.
Visible-Light-Mediated Rose Bengal-Catalyzed α-Hydroxymethylation of Ketones with Methanol
Yang, Jingya,Xie, Dongtai,Zhou, Hongyan,Chen, Shuwen,Duan, Jiaokui,Huo, Congde,Li, Zheng
, p. 3471 - 3476 (2018/09/12)
A visible-light-mediated α-hydroxymethylation of ketones using methanol as the hydroxymethylating reagent has been developed. Using 1 mol% rose bengal as the photosensitizer and air as the green oxidant, the reactions proceeded smoothly at room temperature. Experimental studies indicate the reaction proceeded via a radical pathway. (Figure presented.).
Cobalt-Catalyzed α-Methoxymethylation and Aminomethylation of Ketones with Methanol as a C1 Source
Yang, Jingya,Chen, Shuwen,Zhou, Hongyan,Wu, Chengqi,Ma, Ben,Xiao, Jianliang
supporting information, p. 6774 - 6779 (2018/10/25)
Using methanol as a sustainable C1 source, cobalt-catalyzed α-methoxymethylation and α-aminomethylation of ketones have been developed. With cheap CoCl2·6H2O as catalyst and TBHP as oxidant, the methoxymethylated products were obtained within a short reaction time in up to 91% yield. Based on the observed reversibility of methoxy adduct to enone, the α-aminomethylation of ketones was then achieved by a one-pot methylenation/aza-Michael addition sequence. In addition, an easy way to convert α-methoxymethyl ketones to α-aminomethyl ketones has been discovered.
Catalyzed Reactions of Enol Ethers with SN1 Active Groups: A Novel Method for the Preparation of α-Alkylated Ketones
Gansaeuer, Andreas,Fielenbach, Doris,Stock, Christoph,Geich-Gimbel, Daniel
, p. 1017 - 1030 (2007/10/03)
The performance of tert-alkylations, alkoxyalkylations, and aldehyde enolate allylations proceeding with low catalyst loading (0.1 mol % - 5 mol %) is described. The reactions are complete within short times and can even be performed without solvent and under ambient conditions. The mechanism of the reaction was investigated by deuterium labeling and cross-over studies.
Catalyzed Reactions of Enolates and Cations: A Novel Method for Enolate Alkylation
Gansaeuer, Andreas,Fielenbach, Doris,Stock, Christoph
, p. 845 - 848 (2007/10/03)
The first tertiary alkylations, alkoxyalkylations, and aldehyde enolate allylations are described proceeding with low catalyst loading (0.1 mol % to 5 mol %). The reactions proceed in short times, can be performed without solvent and under ambient conditions.
Azo and Azoxy Compounds: XII. Use of Nitrogen Oxide in Organic Synthesis
Yandovskii,Tselinskii
, p. 147 - 152 (2007/10/03)
Thermal elimination of the alkoxydiazene oxide group from the derivatives of acyl- and benzoylalkanes (cycloalkanes) afforded the corresponding vinyl ketones. Addition of nitrogen oxide and alkoxides to vinyl ketones followed by removal of the acyl group yielded 1,4-dialkoxy-1,2-diazabut-1-ene 2-oxides.
Tris(pentafluorophenyl)boron as an Efficient, Air Stable, and Water Tolerant Lewis Acid Catalyst
Ishihara, Kazuaki,Hanaki, Naoyuki,Funahashi, Miyuki,Miyata, Mayumi,Yamamoto, Hisashi
, p. 1721 - 1730 (2007/10/02)
Tris(pentafluorophenyl)boron is an efficient, air stable, and water tolerant Lewis acid catalyst for the aldol-type and Michael reactions of silyl enol ethers with carbonyl compounds or other electrophiles (trimethyl orthoformate, dimethal acetal, and chloromethyl methyl ether), the allylation reaction of allylsilanes with aldehydes, and the Diels-Alder reaction of dienes with α,β-unsaturated-aldehydes.A solution of formaldehyde in water is applicable as an electrophile.Also, the aldol-type reaction of ketene silyl acetals with aromatic or aliphatic imines is successfully carried out using the same catalyst.
An Efficient and Convenient Method for the Preparation of α-Methylenated Ketones from Silyl Enol Ethers
Hayashi, Masaji,Mukaiyama, Teruaki
, p. 1283 - 1286 (2007/10/02)
In the presence of a catalytic amount of stannous halide, silyl enol ethers react with bromomethyl methyl ether to give the corresponding α-bromoethyl ketones, which are smoothly converted to α-methylenated ketones on the successive addition of tertiary amine by one-pot procedure.This method is successfully applied to a synthesis of sarkomycin intermediate.
Stereoselective Reduction of α-Methyl-β-hydroxy Ketones with Zinc Borohydride
Nakata, Tadashi,Tani, Yoichiro,Hatozaki, Masayoshi,Oishi, Takeshi
, p. 1411 - 1415 (2007/10/02)
Zinc borohydride reduction of α-methyl-β-hydroxy ketones 3 produced the erythro-2-methyl-1,3-glycol derivatives 4 with high stereoselectivity.The selectivity was particularly high when an olefinic group was conjugated to the carbonyl group.Reduction of th
