102613-04-7Relevant articles and documents
An iron-catalyzed hydroalkylation reaction of α,β-unsaturated ketones with ethers
Lan, Yun,Fan, Pei,Liu, Xiao-Wei,Meng, Fei-Fan,Ahmad, Tanveer,Xu, Yun-He,Loh, Teck-Peng
, p. 12353 - 12356 (2017)
A general strategy for the hydroalkylation of vinyl ketones using ethers catalyzed by an iron catalyst is described. This catalytic method permits direct transformation of easily accessible and abundant precursors into highly substituted, structurally diverse and functionally concentrated products.
Synthesis of (R)-(-)-muscone from (R)-5-bromo-4-methylpentanoate: A chiron approach
Shen, Junwei,Shi, Yong,Tian, Weisheng
, p. 683 - 687 (2015)
A synthesis of (R)-muscone (1), a valuable musk odorant, is presented. The stereogenic center of muscone was introduced from methyl (R)-5-bromo-4-methylpentanoate (5), a chiral pool molecule developed in our group, and the macrocyclic ring was prepared by ring-closing metathesis (RCM) reaction. Using methyl (R)-5-bromo-4-methylpentanoate, we have accomplished a synthesis of (R)-muscone, a natural macrocyclic musk, based on chiral pool strategy.
Continuous photochemical generation of catalytically active [CpRu] + complexes from CpRu(η6-C6H6)PF6
Gutierrez, Alicia C.,Jamison, Timothy F.
, p. 6414 - 6417 (2011)
Inter- and intramolecular ene-yne coupling reactions catalyzed by a species generated in situ via photolysis of CpRu(η6-C6H 6)PF6;an inexpensive, readily available, and shelf-stable complex;have been demonstrated under conditions of continuous flow. Importantly, the catalyst can be recovered quantitatively at the end of the reaction. Various functional groups are tolerated by the reaction, which affords skipped diene products in high yields.
Controlling Chemoselectivity of Catalytic Hydroboration with Light
Bergamaschi, Enrico,Chen, Yi-Kai,Hohenadel, Melissa,Lunic, Danijela,McLean, Liam A.,Teskey, Christopher J.
supporting information, (2022/01/13)
The ability to selectively react one functional group in the presence of another underpins efficient reaction sequences. Despite many designer catalytic systems being reported for hydroboration reactions, which allow introduction of a functional handle fo
Methyl Radical Initiated Kharasch and Related Reactions
Tappin, Nicholas D. C.,Renaud, Philippe
, p. 275 - 282 (2020/12/07)
An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).
Chemoselective reduction of aldehydes: Via a combination of NaBH4 and acetylacetone
Sui, Guoqing,Lv, Qingyun,Song, Xiaoqing,Guo, Huihui,Dai, Jiatong,Ren, Li,Lee, Chi-Sing,Zhou, Wenming,Hao, Hong-Dong
supporting information, p. 15793 - 15796 (2019/10/19)
A bench-stable combination of NaBH4-acetylacetone was developed for the efficient chemoselective reduction of aldehydes in the presence of ketones. This method offers a useful synthetic protocol for distinguishing carbonyl reaction sites, and its synthetic utility is reflected by its moisture tolerance and high efficiency in a variety of complex settings.
Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides
Guissart, Céline,Barros, Andre,Rosa Barata, Luis,Evano, Gwilherm
, p. 5098 - 5102 (2018/09/13)
An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.
Preparation method of high-purity 12-methyltridecanal
-
, (2017/07/22)
The invention relates to the field of fine chemical engineering, in particular to a preparation method of high-purity 12-methyltridecanal: 10-undecylenic acid is taken as a raw material, and is subjected to four-step reactions including amidation, Grignard reaction, hydrogenation reduction and alkenyl ozonation. The method has the advantages that the raw material is low in cost and easy to obtain, steps are few, reaction conditions are mild, the impurity content is low, the purification is easy, the reaction repeatability is high, the stability is high, and the method is suitable for industrial mass production.
Aerobic Acetoxyhydroxylation of Alkenes Co-catalyzed by Organic Nitrite and Palladium
Chen, Xian-Min,Ning, Xiao-Shan,Kang, Yan-Biao
supporting information, p. 5368 - 5371 (2016/11/02)
An aerobic acetoxyhydroxylation of alkenes cooperatively catalyzed by organic nitrite and palladium at room temperature using clean and cheap air as the sole oxidant has been developed. Various vicinal diols, diacetoxyalkanes, and dihalogenoalkanes have been synthesized. The gram-scale synthesis has also been approached. Vicinal difluorination and dichlorolation products have also been achieved via this reaction.