68175-34-8Relevant academic research and scientific papers
Regioselective differentiation of vicinal methylene C-H bonds enabled by silver-catalysed nitrene transfer
Scamp, Ryan J.,Scheffer, Bradley,Schomaker, Jennifer M.
supporting information, p. 7362 - 7365 (2019/06/27)
Silver-catalyzed nitrene insertion enables the formation of benzosultams in good yield and with regioselectivity complementary to other transition metal nitrene-transfer catalysts. Preferential formation of six-membered benzosultam rings predominates for alkyl-substituted benzenesulphonamide precursors. Ligand-controlled tunability is also achieved for benzenesulphonamides with γ-branched alkyl substituents. Mechanistic probes suggest that the reaction pathway differs depending on whether a α (benzylic) or β (homobenzylic) C-H bond undergoes amidation, as well as the catalyst identity.
Correction to: Nickel-catalyzed asymmetric reductive cross-coupling to access 1,1-diarylalkanes (Journal of the American Chemical Society (2017) 139 (5684-5687) DOI: 10.1021/jacs.7b01705)
Poremba, Kelsey E.,Kadunce, Nathaniel T.,Suzuki, Naoyuki,Cherney, Alan H.,Reisman, Sarah E.
supporting information, p. 7746 - 7746 (2018/06/26)
Pages 5684 and 5685, Table of Contents, and Supporting Information. The stereochemistry of L1, depicted as the (S,S)- enantiomer in Figure 1, Table 1, the TOC graphic (identical to Figure 1), and the Supporting Information of the original publication, was incorrect. (R,R)-L1 was used in this study. The stereochemistry of (R,R)-L1 has been confirmed by singlecrystal X-ray diffraction; the X-ray diffraction data and CIF file for (R,R)-L1 have been added to the Supporting Information. The corrected TOC graphic/Figure 1 is shown here. (R,R)-L4 and (R,R)-L5 were also used in Table 1 and incorrectly depicted as (S,S)-L4 and (S,S)-L5 in the original publication. To reflect that different enantiomeric series of catalysts were used, Table 1 has been updated to indicate that entries 2, 3, and 6 produce (S)-3a. This correction does not change the stereochemical assignment of the diarylalkane products, or the conclusions of the Communication. The stereochemistry of the products was assigned by obtaining an X-ray structure of diarylalkane 3k, and the rest of the compounds were assigned by analogy. (Table Presented).
Visible-light-mediated anti-regioselective nitrone 1, 3-dipolar cycloaddition reaction and synthesis of bisindolylmethanes
Zheng, Lewei,Gao, Fei,Yang, Chao,Gao, Guo-Lin,Zhao, Yating,Gao, Yuan,Xia, Wujiong
supporting information, p. 5086 - 5089 (2017/11/07)
The development of photoredox reactions of 1, 3- dipolar cycloaddition of nitrones with alkenes is reported. It offers an efficient synthetic method to obtain isoxazolidine derivatives under mild conditions in synthetically useful yields. The nitrones are cyclized with oxidizable styrenes and aliphatic alkenes via a polar radical crossover cycloaddition reaction through photocatalytic reaction without additives. In addition, bis(indole)methanes can also be prepared through this method.
Iron catalyzed methylation and ethylation of vinyl arenes
Zhu, Nengbo,Zhao, Jianguo,Bao, Hongli
, p. 2081 - 2085 (2017/03/09)
Short alkyl chain Heck (type) reactions, especially methyl Heck reactions, are a difficult aspect of the alkyl Heck reaction. To provide a solution to this problem, iron-catalyzed methyl, ethyl and propyl Heck reactions were developed using readily available alkyl peroxides as alkyl sources. The reaction conditions were mild, clean, and easy to handle. No additive was needed, and no hazardous waste was generated. The products were obtained in up to 99% yield of one isomer for most situations. This reaction works for many types of olefin and tolerates a variety of functional groups. Several late-stage functionalizations of natural products and drug molecules were conducted to demonstrate the synthetic applications of this reaction.
Alkene Oxyalkylation Enabled by Merging Rhenium Catalysis with Hypervalent Iodine(III) Reagents via Decarboxylation
Wang, Yin,Zhang, Lei,Yang, Yunhui,Zhang, Ping,Du, Zhenting,Wang, Congyang
supporting information, p. 18048 - 18051 (2014/01/06)
Rhenium-catalyzed oxyalkylation of alkenes is described, where hypervalent iodine(III) reagents derived from widely occurring aliphatic carboxylic acids were used as, for the first time, not only an oxygenation source but also an alkylation source via decarboxylation. The reaction also features a wide substrate scope, totally regiospecific difunctionalization, mild reaction conditions, and ready availability of both substrates. Mechanistic studies revealed a decarboxylation/radical-addition/cation-trapping cascade operating in the reaction.
Practical iron-catalyzed allylations of aryl grignard reagents
Mayer, Matthias,Czaplik, Waldemar M.,Von Wangelin, Axel Jacobi
supporting information; experimental part, p. 2147 - 2152 (2010/12/18)
An operationally simple iron-catalyzed reductive cross-coupling reaction between aryl halides and allyl electrophiles has been developed. The underlying domino process exhibits high versatility with respect to the allylic leaving group (acetate, tosylate, diethyl phosphate, methyl carbonate, trimethylsilanolate, methanethiolate, chloride, bromide) and high economic and environmental sustainability with respect to the catalyst system (0.2-5 mol% tris(acetylacetonato)iron(III), ligand-free) and reaction conditions (tetrahydrofuran, 0°C, 45 min).
Untersuchungen im Wittig-System nach einem ordnenden Konzept auf der Basis alternativer Prinzipien
Bandmann, Heinz,Bartik, Tamas,Bauckloh, Sylvia,Behler, Ansgar,Brille, Frank,et al.
, p. 193 - 204 (2007/10/02)
Our results show that the stereoselectivity of the Wittig-reaction can be controlled by the variation of substituents in accord with the ORDERING CONCEPT OF ALTERNATIV PRINCIPLES (individual pairs, known and unknown classes of alternatives).The "all-phenyl Wittig-system" having three phenyl groups on phosphorous two in ylid- and aldehyd-position was chosen as a standard for our investigations.Differentiation in ylid-position and compensation on phosphorous and aldehyd-position were observed by the comparison of "patterns".Consequently, most of the selectivity rules of Wittig-reactions can be explained by the differentiation through alternatives in the ylid-position.Inversion or conservation of the "patterns" of measured data points to the variation in structure of starting materials, reaction rates and selectivities.Amount-controls were also described in certain systems.
