71787-52-5Relevant academic research and scientific papers
Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
supporting information, (2021/05/31)
A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins
Fernandes, Rodney A.,Ramakrishna, Gujjula V.,Bethi, Venkati
, p. 6115 - 6125 (2020/10/27)
Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.
Copper-Impregnated Magnesium-Lanthanum Mixed Oxide: A Reusable Heterogeneous Catalyst for Allylation of Aldehydes and Ketones
Laha, Soumi,Likhar, Pravin R.,Pogula, Jaya,Sreedhar, B.
supporting information, (2020/02/11)
Copper-impregnated magnesium-lanthanum mixed oxide [Cu(II)/Mg?La] was used as catalyst in synthesis of homoallylic alcohols from aldehydes and ketones using allyltributylstannane as the allylating source. The present protocol provides a great application
Active bismuth mediated allylation of carbonyls/N-tosyl aldimines and propargylation of aldehydes in water
Sawkmie, Micky Lanster,Paul, Dipankar,Khatua, Snehadrinarayan,Chatterjee, Paresh Nath
, (2019/06/08)
Abstract: Active bismuth is synthesized by the chemical reduction of bismuth trichloride using freshly prepared sodium stannite solution as the reducing agent at room temperature. The as-synthesized active bismuth is applied as a reagent for the synthesis of homoallyl alcohol/homopropargyl alcohol from allyl bromide/propargyl bromide and carbonyl compounds in water at 50°C. The homoallyl amines are also synthesized from N-tosyl aldimines and allyl bromide using active bismuth reagent in good yields. No assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere is required for this reaction. The waste bismuth material obtained after the completion of the organic reaction can be reduced to active bismuth by sodium stannite solution and successfully reused for mediating the allylation of aldehydes. Graphical Abstract:: Synopsis Active bismuth mediated allylation/crotylation of aldehydes is developed in water to get homoallyl alcohols. The method is also applied for the allylation of N-tosyl aldimines and propargylation of aldehydes in water to achieve the homoallyl amines and homopropargyl alcohols, respectively. The reactions do not require the assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere.[Figure not available: see fulltext.].
Cationic Cobalt Porphyrin-Catalyzed Allylation of Aldehydes with Allyltrimethylsilanes
Tomifuji, Rei,Masuda, Shota,Kurahashi, Takuya,Matsubara, Seijiro
supporting information, p. 3834 - 3837 (2019/05/24)
Cationic cobalt porphyrin-catalyzed allylation of aldehydes with allyltrimethylsilanes is developed. The formation of the aldehyde-cobalt porphyrin complex, the key intermediate for the addition of allylsilanes, is confirmed by theoretical studies and syn
IDO inhibitors
-
Page/Page column 335; 336, (2018/09/02)
Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.
Bi-mediated allylation of aldehydes in [bmim][Br]: A mechanistic investigation
Koli, Mrunesh,Chatterjee, Sucheta,Chattopadhyay, Subrata,Goswami, Dibakar
supporting information, p. 2198 - 2203 (2018/09/04)
The inexpensive room temperature ionic liquid (RTIL), [bmim][Br] has been found to be a superior medium for the Bi-mediated Barbier-type allylation of aldehydes compared to other conventional solvents. It plays the dual role of a solvent and a metal activ
An organoantimony complex with intramolecular N?→?Sb coordination as effective and recyclable catalyst for the allylation of aldehydes with tetraallyltin
Tan, Nianyuan,Nie, Tong,Au, Chak-Tong,Lan, Donghui,Wu, Shuisheng,Yi, Bing
supporting information, p. 2592 - 2595 (2017/06/13)
An air-stable hypervalent organoantimony (III) triflate complex (PhN(CH2C6H4)2SbOSO2CF3) having intramolecular N?→?Sb coordination was synthesized and characterized by techniques such as s
A Green approach for allylations of aldehydes and ketones: Combining allylborate, mechanochemistry and lanthanide catalyst
De Souza, Viviane P.,Oliveira, Cristiane K.,De Souza, Thiago M.,Menezes, Paulo H.,Alves, Severino,Longo, Ricardo L.,Malvestiti, Ivani
, (2016/12/02)
Secondary and tertiary alcohols synthesized via allylation of aldehydes and ketones are important compounds in bioactive natural products and industry, including pharmaceuticals. Development of a mechanochemical method using potassium allyltrifluoroborate salt and water, to successfully perform the allylation of aromatic and aliphatic carbonyl compounds is reported for the first time. By controlling the grinding parameters, the methodology can be selective, namely, very efficient for aldehydes and ineffective for ketones, but by employing lanthanide catalysts, the reactions with ketones can become practically quantitative. The catalyzed reactions can also be performed under mild aqueous stirring conditions. Considering the allylation agent and its by-products, aqueous media, energy efficiency and use of catalyst, the methodology meets most of the green chemistry principles.
A Mild, efficient protocol for the synthesis of homoallylic alcohols using potassium allyltrifluoroborate promoted by salicylic acid
Silva, Jadson F.,Lima, Josefa A.C.,De Freitas, Jucleiton J.R.,Freitas, Ladjane P.S.R.,Menezes, Paulo H.,Freitas, Juliano C.R.
, p. 49 - 57 (2015/12/31)
Background: In the current decade, organotrifluoroborates have attained remarkable development in Chemistry and Materials. This can be evidenced by the increasing number of articles, review articles and patents devoted to this subject. As a consequence, the number of citations derived from papers dealing with this subject has experienced an exponential growth in the last years. The aim of this paper to describe a methodology based on the use of potassium allyltrifluoroborate for the synthesis of homoallylic alcohols using water as a co-solvent and under mild reaction conditions. Methods: The methodology is very robust (wide range of aldehydes) and simple, it uses low catalyst loadings and it is synthetically useful because it could be applied for the synthesis of more complex compounds. In addition, detailed experimental procedures, including the preparation of the starting materials, as well as the corresponding 1H, 13C, 19F and 11B spectra for all synthesized compounds are provided. Results: The method is environmentally friendly while it uses water as a solvent and the desired compounds containing different functionalities were obtained in moderate to good yields (60-93%) without the need of further purification in a very chemo- and regioselective way. Conclusion: Salicylic acid can efficiently promote the allylation of aldehydes using potassium allyltrifluoroborate at room temperature to yield the corresponding homoallylic alcohols in moderate to good yields. The method is efficient and environmentally friendly while it uses water as co-solvent. In addition the method is regio- and chemoselective and could be applied in the synthesis of more complex homoallylic alcohols.
