180037-65-4Relevant articles and documents
Designing a bifunctional metal-organic framework by tandem post-synthetic modifications; an efficient and recyclable catalyst for Suzuki-Miyaura cross-coupling reaction
Hamadi, Hosein,Nobakht, Valiollah,Salahshournia, Behrang
, (2020)
A new Cu/Pd bimetallic Cu-MOF-[Pd] was synthesized through covalent, dative and inorganic post-synthetic modifications. In order to achieve the Cu-MOF-[Pd], Zn-MOF (TMU-17-NH2) was initially selected and fabricated by grafting of salicylaldehyde via Schiff-base formation followed by complex formation with Pd(II). Then, the as-synthesis MOF, Zn-MOF-[Pd], was subjected as 3D-template to obtain Cu-MOF-[Pd] by transmetalation process. The Cu-MOF-[Pd] was characterized by FT-IR spectroscopy, atomic absorption spectroscopy (AAS), field emission scanning electron microscopy (FE-SEM), powder X-ray diffraction (PXRD), energy dispersive X-ray spectroscopy (EDS), and EDS mapping techniques. The feasibility of using Cu-MOF-[Pd] as a highly active recoverable catalyst was confirmed in the Suzuki–Miyaura cross-coupling reaction in a mixed water/ethanol solvent. The results show that this novel nano-composite could serve as an efficient bimetallic heterogeneous catalyst and reuse at least for 5 times without loss in activity.
One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping
Yamane, Daichi,Tanaka, Haruna,Hirata, Akihiro,Tamura, Yumiko,Takahashi, Daichi,Takahashi, Yusuke,Nagamitsu, Tohru,Ohtawa, Masaki
supporting information, p. 2831 - 2835 (2021/05/05)
A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.
Efficient hydrogenation of levulinic acid catalysed by spherical NHC-Ir assemblies with atmospheric pressure of hydrogen
Liu, Yaoqi,Lu, Zeye,Shen, Lingyun,Tu, Tao,Wu, Jiajie,Zheng, Qingshu
supporting information, p. 5037 - 5042 (2021/07/29)
A practical, efficient, and mild hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) under 1 atm H2was realized by single-sited 3D porous self-supported N-heterocyclic carbene iridium catalysts. Quantitative yields and selectivities were achieved at 0.02 mol% catalyst loading, and the catalyst could be reused for 9 runs without obvious loss of selectivity or activity.
Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids
Xu, Xiao-Long,Li, Zhi
supporting information, p. 5078 - 5081 (2019/09/03)
Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.
Synthesis of Enantiopure γ-Lactones via a RuPHOX-Ru Catalyzed Asymmetric Hydrogenation of γ-Keto Acids
Li, Jing,Ma, Yujie,Lu, Yufei,Liu, Yangang,Liu, Delong,Zhang, Wanbin
, p. 1146 - 1153 (2019/01/30)
A RuPHOX?Ru catalyzed asymmetric hydrogenation of γ-keto acids has been developed, affording the corresponding enantiopure γ-lactones in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 10000 S/C) under the indicated reaction conditions and the resulting products can be transformed to several enantiopure building blocks, biologically active compounds and enantiopure drugs. (Figure presented.).
Nucleo-Palladation-Triggering Alkene Functionalization: A Route to γ-Lactones
Zheng, Meifang,Chen, Pengquan,Huang, Liangbin,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 5756 - 5759 (2017/11/10)
An unprecedented strategy for the highly effective synthesis of γ-lactones from homoallylic alcohols was achieved by palladium catalysis in one step. The protocol affords aryl, alkyl, and spiro γ-lactones directly from readily available homoallylic alcohols in good yields with excellent functional group tolerance and high chemoselectivity under mild conditions.
Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams
Kise, Naoki,Hamada, Yusuke,Sakurai, Toshihiko
, p. 1143 - 1156 (2017/02/18)
The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.
Efficient Hydrogenation of Biomass Oxoacids to Lactones by Using NHC–Iridium Coordination Polymers as Solid Molecular Catalysts
Liu, Yaoqi,Sun, Zheming,Huang, Changyu,Tu, Tao
, p. 355 - 360 (2017/02/05)
A series of NHC–iridium coordination polymers have proven to be robust, efficient and recyclable solid molecular catalysts toward the hydrogenation of biomass levulinic acid (LA) to γ-valerolactone. Along with quantitative yields attained at 0.01 mol % catalyst loading under 50 atm of H2, the solid molecular catalyst was readily recovered and reused for 12 runs without obvious loss of the selectivity and activity. Remarkably, up to 1.2×105 TON, an unprecedented value could be achieved in this important transformation. In addition, a number of LA homologues, analogues and derivatives were well tolerated to deliver various intriguing and functional lactones in good to excellent yields, which further confirmed the feasibility of the solid molecular catalysts.
MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones
Wu, Lihuan,Zhang, Zhenming,Liao, Jianhua,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 2628 - 2631 (2016/02/18)
An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.
Copper-catalyzed intermolecular oxidative [3 + 2] cycloaddition between alkenes and anhydrides: A new synthetic approach to γ-lactones
Huang, Liangbin,Jiang, Huanfeng,Qi, Chaorong,Liu, Xiaohang
supporting information; experimental part, p. 17652 - 17654 (2011/03/16)
A new copper-catalyzed oxidative [3 + 2] cycloaddition of alkenes with anhydrides using oxygen as the sole oxidant to afford γ-lactones has been developed. This catalyzed cyclization process has a broad substrate scope and affords γ-lactones in good to excellent yields.
