25333-24-8Relevant academic research and scientific papers
3,6-bis(triphenylphosphonium)cyclohexene peroxodisulfate: A highly efficient oxidant for the selective oxidation of benzylic alcohols
Badri,Shalbaf,Heidary
, p. 3473 - 3479 (2001)
The synthesis of 3,6-bis(triphenylphosphonium)cyclohexene peroxodisulfate and its application for the selective oxidation of benzylic alcohols is reported.
Reaction of iron aminocarbene complexes with electronically deficient alkenes
Rotrekl, Ivan,Vyklicky, Libor,Dvorák, Dalimil
, p. 329 - 333 (2001)
Thermal reaction of iron aminocarbene complexes bearing aromatic substituent (CO)4Fe=C(Ar)N(CH3)2 with methyl acrylate, acrylonitrile and methyl vinyl ketone furnishes 1,4-dicarbonyl compounds - formal products of Michael
LIGHT INDUCED CATALYTIC C-H OXYGENATION OF ALKANES
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Paragraph 00219, (2021/04/02)
A method of oxygenating a benzylic C-H bond is provided. The method comprises light induced activation of an initiator and subsequent reaction with oxygen, resulting in the formation of free radicals. Subsequently, free radicals catalyze the reaction of the benzylic C-H bond with oxygen, thereby forming an oxygenated compound.
Visible-Spectrum Solar-Light-Mediated Benzylic C-H Oxygenation Using 9,10-Dibromoanthracene As an Initiator
Santra, Sourav K.,Szpilman, Alex M.
, p. 1164 - 1171 (2020/12/23)
We report a visible-light-mediated benzylic C-H oxygenation reaction. The reaction is initiated by solar light or the blue LED activation of 9,10-dibromoanthracene in a reaction with oxygen and takes place at ambient temperature and air pressure. Secondary benzylic positions are oxygenated to ketones, while tertiary benzylic carbons are oxygenated to give hydroperoxides. Notably, cumene hydroperoxide is produced in a higher yield and at milder conditions than the currently employed industrial conditions.
Photoinduced Deaminative Alkylation for the Synthesis of γ-Ketoesters via Electron Donor–Acceptor Complex Formation
Wang, Jia-Xin,Ge, Wei,Xing, Wei-Long,Fu, Ming-Chen
supporting information, p. 18224 - 18231 (2021/12/13)
Visible-light-induced deaminative alkylation of Katritzky salts with silyl enol ethers has been developed. The reaction can proceed efficiently through electron donor–acceptor complex formation, avoiding the use of precious metal complexes or synthetically elaborate organic dyes. A series of functionalized γ-ketoesters was successfully obtained with good functional group tolerance and compatibility under mild and straightforward conditions.
Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He
, p. 4327 - 4337 (2021/05/31)
A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is
Tandem homologation-acylation chemistry: Single and double homologation
Henderson, Carley S.,Mazzone, Jennifer R.,Moore, Amanda M.,Zercher, Charles K.
supporting information, (2021/06/01)
Treatment of β-dicarbonyls with the Furakawa-variant of the Simmons-Smith reagent results in homologation and production of an intermediate zinc enolate. Treatment of the enolate with various acylating agents generate products with both γ-dicarbonyl funct
Transition Metal-Free Alkyne-Aldehyde Reductive C?C Coupling trough Cascade Borylation/Olefin Isomerization
Khan, Imran,Luo, Zhibin,Xu, Yin,Xie, Jimin,Zhu, Weihua,Liu, Bin
, (2020/05/04)
A direct approach to γ-keto esters through cascade alkyne-aldehyde reductive C?C coupling of propargyl esters and aromatic aldehydes under transition-metal-free (TM-free) fashion was developed. Compared with multistep processes, this procedure provides a
Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters
Shi, Yongjie,Tan, Xuefeng,Gao, Shuang,Zhang, Yao,Wang, Jingxin,Zhang, Xumu,Yin, Qin
supporting information, p. 2707 - 2713 (2020/03/30)
Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.
Biocatalytic Asymmetric Reduction of γ-Keto Esters to Access Optically Active γ-Aryl-γ-butyrolactones
??d?o-Dobrowolska, Anna,Borowiecki, Pawe?,Heider, Johann,Kroutil, Wolfgang,Reiter, Tamara,Schühle, Karola,Szaleniec, Maciej,Tataruch, Mateusz,Telatycka, Natalia
, (2020/04/20)
An efficient stereoselective syntheses of a series of functionalized optically active γ-aryl-γ-butyrolactones is achieved by enzymatic asymmetric reduction of the corresponding sterically demanding γ-keto esters employing wild-type and recombinant alcohol dehydrogenases. The best stereoselectivities for the reduction via hydrogen transfer was obtained with two short chain dehydrogenases (SDRs) of complementary stereospecificity from Aromatoleum aromaticum, namely the Prelog-specific NADH-dependent (S)-1-phenylethanol dehydrogenase [(S)-PED] and the anti-Prelog-specific (R)-1-(4-hydroxyphenyl)-ethanol dehydrogenase [(R)-HPED], respectively.Biotransformations catalyzed by both enzymes, followed by TFA-catalyzed cyclization of the resulting γ-hydroxy esters, furnished the respective (S)- and (R)-configured products with exquisite optical purity (up to >99% ee). The synthetic value was demonstrated on preparative scale for the asymmetric bioreduction of the model compound, methyl 4-oxo-4-phenylbutanoate, affording optically pure (S)-γ-phenyl-γ-butyrolactone (>99% ee) in 67–74% isolated yield at 89–95% conversion depending on the applied scale. (Figure presented.).
