87722-64-3Relevant academic research and scientific papers
Umpolung Strategy for Arene C?H Etherification Leading to Functionalized Chromanes Enabled by I(III) N-Ligated Hypervalent Iodine Reagents
Mikhael, Myriam,Guo, Wentao,Tantillo, Dean J.,Wengryniuk, Sarah E.
supporting information, p. 4867 - 4875 (2021/09/14)
The direct formation of aryl C?O bonds via the intramolecular dehydrogenative coupling of a C?H bond and a pendant alcohol represents a powerful synthetic transformation. Herein, we report a method for intramolecular arene C?H etherification via an umpoled alcohol cyclization mediated by an I(III) N-HVI reagent. This approach provides access to functionalized chromane scaffolds from primary, secondary and tertiary alcohols via a cascade cyclization-iodonium salt formation, the latter providing a versatile functional handle for downstream derivatization. Computational studies support initial formation of an umpoled O-intermediate via I(III) ligand exchange, followed by competitive direct and spirocyclization/1,2-shift pathways. (Figure presented.).
Nickel-Catalyzed Hydrogen-Borrowing Strategy for α-Alkylation of Ketones with Alcohols: A New Route to Branched gem-Bis(alkyl) Ketones
Das, Jagadish,Singh, Khushboo,Vellakkaran, Mari,Banerjee, Debasis
supporting information, p. 5587 - 5591 (2018/09/25)
The α-alkylation of ketones using an earth-abundant and nonprecious NiBr2/L1 system is reported. This nickel-catalyzed reaction could be performed in gram scale and successfully applied in the synthesis of donepezil (Alzheimer's drug) and functionalization of steroid hormones and fatty acid derivatives. Synthesis of N-heterocycles, methylation of ketones, and one-pot double alkylation to bis-hetero aryl ketones using two different alcohols with a single catalyst broadens the scope of the catalytic protocol. Preliminary mechanistic studies using defined Ni-H species and deuterium-labeling experiments established the participation of the borrowing-hydrogen strategy.
Liquid-Liquid Extraction Protocol for the Removal of Aldehydes and Highly Reactive Ketones from Mixtures
Boucher, Maria M.,Furigay, Maxwell H.,Quach, Phong K.,Brindle, Cheyenne S.
, p. 1394 - 1403 (2017/09/23)
The reaction of the bisulfite ion with aldehydes to form charged bisulfite adducts is a well-established method for the purification of aldehydes. This reaction has been modified to create a convenient liquid-liquid extraction method for the removal of aldehydes from mixtures. The use of a water-miscible solvent allows the reaction to occur during a simple 30 s shaking protocol by increasing the contact between the bisulfite ion and the aldehyde. The introduction of an immiscible solvent allows for the extraction of the uncharged organic components away from the bisulfite adduct. The developed protocol is applicable to a wide range of aldehydes, including sterically hindered neopentyl aldehydes. Sterically unhindered cyclic and linear ketones, as well as highly electrophilic ketones, are also removed using this protocol. The mild conditions tolerate a wide range of functional groups, allowing for excellent aldehyde contaminant removal rates with high levels of recovery of the desired component.
New methylene homologation method for cyclic ketones
Liu, Huaqing,Sun, Chunrui,Lee, Nam-Kyu,Henry, Roger F.,Lee, Daesung
, p. 11889 - 11893 (2012/10/29)
Teaching new tricks to an old dog: By intercepting adducts between ketones and lithium trimethylsilyldiazomethane, a new Tiffeneau-Demjanov type methylene homologation could be realized in a single-step operation. Among proton sources and Lewis acids, silica gel was found to be the most effective reagent for the protonation of intermediates and their subsequent ring expansion (see scheme). Copyright
Quantitative comparison of chiral catalysts selectivity and performance: A generic concept illustrated with cyclododecanone monooxygenase as baeyer-villiger biocatalyst
Fink, Michael J.,Rial, Daniela V.,Kapitanova, Petra,Lengar, Alenka,Rehdorf, Jessica,Cheng, Qiong,Rudroff, Florian,Mihovilovic, Marko D.
supporting information, p. 3491 - 3500 (2013/02/22)
Within this work a generic tool for chiral catalyst evaluation is established based on the application-oriented properties activity and selectivity; the concept aims at quantitatively comparing catalyst performance in general on a multitude of substrates.
Indium metal as a reducing agent. Selective reduction of the carbon-carbon double bond in highly activated conjugated alkenes
Ranu, Brindaban C.,Dutta, Jyotirmoy,Guchhait, Sankar K.
, p. 2603 - 2605 (2007/10/03)
(Equation presented) Indium metal in aqueous ethanolic ammonium chloride reduces the C=C bond in highly activated conjugated alkenes such as α,α-dicyano olefins, β-arylenones, and enone esters.
Synthesis of certain unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9- endo-(aralkyl)-tricyclo [5.2.1.02,6 decane-8-ketoxime esters and ethers with local anesthetic and analgesic activities
Aboul-Enein M, Nabil,El-Azzouny, Aida,Abdallah, Nevine A.,Maklad, Yousreya A.,Saleh, Ola A.,Ebeid
, p. 197 - 208 (2007/10/03)
The synthesis of series of unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9-endo-(aralkyl)tricyclo [5.2.1.0(2,6)] decane-8-ketoximes esters and ethers 3a-j, 4a-d, 7a-j and 13a-d from the oxime synthons 2, 6a-e, 12a and 12b, respectively, is described. Al
Regioselective Aryl Radical Cyclization. 1. Stereocontrolled Synthesis of Linearly Condensed Hydroaromatic Carbocyclic Systems through 6-endo-ring Closures
Pal, Sitaram,Mukhopadhyaya, Jayanta K.,Ghatak, Usha Ranjan
, p. 2687 - 2694 (2007/10/02)
The stereocontrolled synthesis of trans-octahydroanthracenes 3, 11a-c, and 14a-c and trans-octahydro-5aH-cycloheptanaphthalene (27) through implementation of an efficient and highly regioselective 6-endo-trig-aryl radical cyclization of the respective 2-(o-bromoaryl)-1-methylenecyclohexanes 2, 10a-c, and 13a-c and 2-(o-bromobenzyl)-1-methylenecycloheptane (41) with tri-n-butyltin hydride id described.The radical cyclization of 2-(o-bromobenzyl)-1-methylenecyclopentane (43), in contrast, produced a mixture of the cis- and trans-hexahydro-1H-benzindenes (38) and (37).
