20157-18-0Relevant academic research and scientific papers
1,7-Di-tert-butyl-Substituted aza-BODIPYs by Low-Barrier Rotation to Enhance a Photothermal-Photodynamic Effect
Su, Yajun,Hu, Qiao,Zhang, Dongxiang,Shen, Yue,Li, Sicheng,Li, Ran,Jiang, Xin-Dong,Du, Jianjun
supporting information, (2021/11/16)
1,7-Di-tert-butyl-substituted aza-BODIPYs (tBu-azaBDP) were successfully obtained for the first time. The structures of tBu-azaBDP and Ph-azaBDP were confirmed by X-ray crystal analysis, and tBu-azaBDP 2 is more twisted than Ph-azaBDP 5. tBu-azaBDPs have significant photo-stability and enhanced water solubility. tBu-azaBDPs possess excellent optical properties, such as high molar extinction coefficients, broad full width half maxima, and large Stokes shifts, which is comparable to those of the parent dye Ph-azaBDP. Although the low-barrier rotation of the distal -tBu groups in tBu-azaBDPs results in low quantum yield, photothermal conversion efficiency and singlet oxygen generation ability of tBu-azaBDPs are more effective than those of Ph-azaBDP, which is highly desirable for a photothermal-photodynamic therapy agent.
Direct Access to α,β-Unsaturated Ketones via Rh/MgCl2-Mediated Acylation of Vinylsilanes
Chen, Zi-Yan,Deng, Xue-Zu,Song, Yang,Xue, Fei,Yamane, Motoki,Yue, Yan-Ni
, p. 12693 - 12704 (2021/09/28)
We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized with synthetically useful yield.
Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes
Seo, Sangwon,Gao, Ming,Paffenholz, Eva,Willis, Michael C.
, p. 6091 - 6098 (2021/05/29)
We demonstrate that aryltriazenes can promote three distinctive types of C-H functionalization reactions, allowing the preparation of complex benzene molecules with diverse substitution patterns. 2-Triazenylbenzaldehydes are shown to be efficient substrates for Rh(I)-catalyzed intermolecular alkyne hydroacylation reactions. The resulting triazene-substituted ketone products can then undergo either a Rh(III)-catalyzed C-H activation, or an electrophilic aromatic substitution reaction, achieving multifunctionalization of the benzene core. Subsequent triazene derivatization provides traceless products.
TBu--azaBODIPY photo-thermal dye and preparation method thereof
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Paragraph 0023-0024, (2021/08/11)
The invention discloses a tBu--azaBODIPY photo-thermal dye and a preparation method thereof, and relates to a photo-thermal dye and a preparation method thereof. The general formula of the dye is as shown in the formula I which is shown in the description
Enantioselective Conjugate Azidation of α,β-Unsaturated Ketones under Bifunctional Organocatalysis by Direct Activation of TMSN3
Humbrías-Martín, Jorge,Pérez-Aguilar, M. Carmen,Mas-Ballesté, Rubén,Dentoni Litta, Antonella,Lattanzi, Alessandra,Della Sala, Giorgio,Fernández-Salas, Jose A.,Alemán, José
, p. 4790 - 4796 (2019/09/16)
An enantioselective organocatalytic conjugate azidation of α,β-unsaturated ketones is presented. A bifunctional organocatalyst activates TMSN3, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre-formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst. (Figure presented.).
Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
supporting information, p. 2003 - 2006 (2018/04/16)
A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p
One-pot synthesis of [4-(tert-butyl)-1H-pyrrol-3-yl](phenyl)methanone from tosylmethyl isocyanide and carbonyl compound
Kaur, Ramandeep,Kumar, Kapil
, p. 700 - 702 (2018/09/19)
[Figure not available: see fulltext.] An efficient one-pot synthetic procedure for [4-(tert-butyl)-1H-pyrrol-3-yl](phenyl)methanone was elaborated using acetophenone and trimethylacetaldehyde in the presence of TosMIC and mild base LiOH·H2O. Th
Direct β-Alkylation of Ketones and Aldehydes via Pd-Catalyzed Redox Cascade
Wang, Chengpeng,Dong, Guangbin
supporting information, p. 6057 - 6061 (2018/05/14)
We report a direct β-alkylation of ketones and aldehydes with simple alkyl bromides through a Pd-catalyzed redox-cascade strategy. The use of a Cu cocatalyst is important for improved efficiency. The reaction is redox-neutral, without the need for strong acids or bases. Both cyclic and acyclic ketones, as well as α-branched aldehydes, are suitable substrates for coupling with secondary and tertiary alkyl bromides. Concise formal synthesis of Zanapezil is achieved using this β-alkylation method.
Chloramphenicol base chemistry. Part 11: chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones
Yan, Linjie,Wang, Haifeng,Xiong, Fangjun,Tao, Yuan,Wu, Yan,Chen, Fener
, p. 921 - 929 (2017/07/11)
The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various α,β-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X7 receptor antagonists.
Barluenga's reagent with HBF4 as an efficient catalyst for alkyne-carbonyl metathesis of unactivated alkynes
Murai, Kosuke,Tateishi, Keiichiro,Saito, Akio
supporting information, p. 10352 - 10356 (2016/11/18)
Barluenga's reagent (IPy2BF4, Py = pyridine) treated with HBF4 efficiently catalyzes the inter- and intramolecular alkyne-carbonyl metathesis of unactivated alkynes with aldehydes or ketones, most of which proceed at room temperature. This work represents the first catalytic application of the Barluenga's reagent.
