58369-45-2Relevant articles and documents
Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation
Liou, Yan-Cheng,Su, Yin-Hsiang,Ku, Kuan-Chun,Edukondalu, Athukuri,Lin, Chun-Kai,Ke, You-Syuan,Karanam, Praneeth,Lee, Chia-Jui,Lin, Wenwei
supporting information, p. 8339 - 8343 (2019/10/16)
We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.
An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources
Chen, Pei,Zhang, Qian-Qian,Guo, Jia,Chen, Lu-Lu,Wang, Yan-Bo,Zhang, Xiao
, p. 6958 - 6966 (2018/10/02)
An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.
Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones: Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones
He, Zhen,Qi, Xiaotian,She, Zhijie,Zhao, Yinsong,Li, Shiqing,Tang, Junbin,Gao, Ge,Lan, Yu,You, Jingsong
supporting information, p. 1403 - 1411 (2017/02/10)
A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.
Transition-metal-free formal decarboxylative coupling of ?±-oxocarboxylates with ?±-bromoketones under neutral conditions: A simple access to 1,3-diketones
He, Zhen,Qi, Xiaotian,Li, Shiqing,Zhao, Yinsong,Gao, Ge,Lan, Yu,Wu, Yiwei,Lan, Jingbo,You, Jingsong
supporting information, p. 855 - 859 (2015/02/05)
A transition-metal-free formal decarboxylative coupling reaction between ?±-oxocarboxylates and ?±-bromoketones to synthesize 1,3-diketone derivatives is presented. In this reaction, a broad scope of substrates can be employed, and neither a metal-based reagent nor an additional base is required. DFT calculations reveal that this reaction proceeds through a coupling followed by decarboxylation mechanism and the ?±-bromoketone unprecedentedly serves as a nucleophile under neutral conditions. The rate-determining step is an unusual hydrogen-bond-assisted enolate formation by thermolysis.
MgBr2·OEt2-promoted coupling of ketones and activated acyl donors via soft enolization: A practical synthesis of 1,3-diketones
Lim, Daniel,Zhou, Guoqiang,Livanos, Alexandra E.,Fang, Fang,Coltart, Don M.
scheme or table, p. 2148 - 2152 (2009/04/03)
Ketones undergo soft enolization and acylation on treatment with MgBr 2OEt2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-pentafluorophenyl esters, and, in these cases, is conducted using untreated, reagent grade CH2C12 open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds. Thieme Stuttgart.
Direct carbon - Carbon bond formation via soft enolization: A facile and efficient synthesis of 1,3-diketones
Lim, Daniel,Fang, Fang,Zhou, Guoqiang,Coltart, Don M.
, p. 4139 - 4142 (2008/02/12)
Ketones undergo soft enolate formation and acylation on treatment with MgBr2·OEt2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-Pfp esters, and, in these cases, is conducted with untreated, reagent-grade CH2Cl2 open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds.
γ,δ-unsaturated β-diketones by acylation of ketones
Katritzky, Alan R.,Meher, Nabin K.,Singh, Sandeep K.
, p. 7792 - 7794 (2007/10/03)
γ,δ-Unsaturated β-diketones have been prepared by the acylation of ketones with N-acylbenzotriazoles of various aliphatic and aromatic α,β-unsaturated carboxylic acids.
