Over-oxidation was not observed in case of bi- and tri-cyclic-1-pyrrolines. Makra Z., Pusks L. G., Kanizsai I. Any product that may be evaluated in this article, or claim that may be made by its manufacturer, is not guaranteed or endorsed by the publisher. Careers. Copyright Authors also attempted on large-scale synthetic applications employing readily recoverable IBX-supported on polystyrene (PSS-IBX). Received 2021 Dec 22; Accepted 2022 Jan 11. A polar aprotic solvent such as acetonitrile provided high yields of the desired compound. IBX/TEAB-mediated Oxidative Dimerization of Thioamides: Synthesis of 3,5-disubstituted 1,2,4-thiadiazoles. Metal-free Synthesis of 2-aminobenzoxazoles Using Hypervalent Iodine Reagent, Synthesis of 4-Chloroisocoumarins via Intramolecular Halolactonization of O-Alkynylbenzoates: PhICl2-Mediated C-O/C-Cl Bond Formation, Advances in Synthetic Applications of Hypervalent Iodine Compounds. It is also useful for utilizing highly diverse Mannich substrates/intermediates for oxidative C (sp3)-functionalization, with a further derivatization potential. Authors designed this interesting domino reaction between -enamino esters 16) and allyl alcohols 17) utilizing 2-iodoxybenzoic acid as an oxidant and carried out reactions in the DMSO medium (Supplementary Figures S7,S8). (2014). cookies. presented an expeditious one-pot-approach for a-keto-1,3,4-oxadiazoles 61) mediated by IBX/tetraethyl ammonium bromide in an oxidative cyclization of hydrazidehydrazones (9c), which were produced in situ from the reaction of hydrazides (9b) and aryl glyoxals 62) under mild conditions (Supplementary Figures S22,S23) (Kumar et al., 2014). About Iodobenzoic Acid. During optimization studies, authors examined the feasibility and effects of different temperature conditions and stoichiometries. Kamlesh Kumar et al. l Several oxidants including IBX, NBS, urea-hydrogen peroxide (UHP), tert-butyl hydroperoxide, m-chloroperoxybenzoic acid, and benzoyl peroxide were evaluated in the optimization process. Authors noticed that in the absence of -CD, these reactions did not result in satisfactory yields of the aromatized products. The Journal of Organic Chemistry 2020, 85 (2) , . Dalip Kumar et al. HHS Vulnerability Disclosure, Help Zsofia Makra et al. The aliphatic and heteroaromatic substituents at C 1) also did not hinder the reaction. J. Nat. During optimization studies, authors examined the feasibility and effects of different temperature conditions and stoichiometries. 16, 62746277. The reactions proceeded with high regioselectivity with regard to C-3 position of indolizines (67), since C-1 position was less nucleophilic than C-3. Download scientific diagram | Scheme 4. 26, 17271732. The electron-donating groups at C 1) afforded higher yields. [structure: see text] Catalytic use of o-iodoxybenzoic acid (IBX) in the presence of Oxone as a co-oxidant is demonstrated for the oxidation of primary and secondary alcohols in user- and eco-friendly solvent mixtures. Pravin Patil et al. 2009 Jan 14;131(1):251-62. doi: 10.1021/ja807110n. of AcOH in acetonitrile solvent (Supplementary Figure S33) (Lin and Lu, 2010). Chem Commun (Camb). The desired products were obtained in the range of 5096%. These moieties represent different and divergent classes of molecules such as drugs, amino acids, and dye stuffs; a large number of heterocyclic compounds are known in the literature and are being synthesized regularly. High regioselectivity was observed in the product formation. Authors evaluated the scope of various tryptophan analogs 81). (2019). Many reactions with IBX are performed in DMSO, due to solubility. doi:10.1055/s-0035-1560416, Silva, T. S., Zeoly, L. A., and Coelho, F. (2020). Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of - PubMed Hyatt I. F. D., Dave L., David N., Kaur K., Medard M., Mowdawalla C. (2019). IBX in Aqueous Medium: a green Protocol for the Biginelli Reaction. Following the same synthetic strategy, Mannich substrates related to pyridine 38) and pyrazine ring systems were also investigated successfully to access highly diverse cyclic compounds imidazo [1,2-a]pyridines (39) and imidazo [1,2-a]pyrazines (40) with moderate to good yields (Supplementary Figure S17). During optimization studies, the effect of polar aprotic, polar protic, and nonpolar solvents was also examined. 17, 78227848. IBX Mediated Reaction of -enamino Esters with Allylic Alcohols: a One Pot Metal Free Domino Approach to Functionalized Pyridines. It is followed by IBX-supported oxidative aromatization affording the title compounds. These are proved to be unique in conducting many important rearrangement reactions providing useful building blocks. doi:10.1055/s-0033-1340981, Kumar, K., Joshi, P., and Rawat, D. S. (2021). In the first step of this cascade process, propargyl vinyl ethers 3) formed corresponding allenyl carbonyl compounds in the presence of low catalyst loadings of AgSbF6 at 23C, without any significant by-product formation. 2019, 16871714. Tetrahedron Lett. 43, 953962. This site needs JavaScript to work properly. Narayana Murthy and Nageswar explored o-iodoxybenzoic acid as an efficient and mild oxidizing agent for aromatizing diversely substituted 1-benzylpyrrolidines (108) and N-substituted l-proline analogs (110) in the aqueous medium assisted by the supramolecular host -CD under room temperature conditions (Supplementary Figures S39,S40) (Murthy and Nageswar, 2011). An efficient mild one-pot sequential multi-component approach for providing an easy access to N-aryl-pyrrole-3-carbaldehydes 28) under metal-free conditions was accomplished by (Supplementary Figures S13,S14) Singh et al. Patil P., Nimonkar A., Akamanchi K. G. (2014). 2009 Aug 7;74(15):5405-10. doi: 10.1021/jo9009003. The reaction mechanism for the product formations was explained appropriately. Iodosyl benzene (PhIO) iodobenzene dichloride (PhICl2), iodobenzene diacetate (PhI(OAc)2), iodine trifluoroacetate [(PhI(OCOCF3)]2, Kosers reagent-hydroxy (tosyloxy) iodobenzene (PhI(OTS)OH) (HTIB), DessMartin periodinane (DMP), and 2-iodoxybenzoic acid (IBX) are the widely used hypervalent iodine reagents for organic transformations (Dong et al., 2014; Sun and Shi, 2014; Charpentier et al., 2015; Li et al., 2016; Yoshimura and Zhdankin, 2016; Hyatt et al., 2019), due to the mild reaction conditions and transition metal-free nature and operational simplicity. Several antioxidants and anti-influenza moieties containing pyrogallol 44) and catechol structures were made by Bruno. It was reported that 60% of IBX was recovered and reused without loss of activity for some of the following reaction cycles. Gonzlez-Zamora E., Islas-Jcome A., Gutirrez-Carrillo A., Garca-Garibay M. (2014). IBXMediated Oxidation of Primary Alcohols and Aldehydes To Form Carboxylic Acids Mazitschek, Ralph; Mlbaier, Marcel; Giannis, Athanassios Angewandte Chemie International Edition , Volume 41 (21) - Jan 4, 2002 Read Article Download PDF Share Full Text for Free 3 pages Article Details Recommended References Bookmark Add to Folder Cite Social 55, 44364454. Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation. Narayana Murthy and Nageswar explored o-iodoxybenzoic acid as an efficient and mild oxidizing agent for aromatizing diversely substituted 1-benzylpyrrolidines (108) and N-substituted doi:10.1039/C4OB00318G, Gade, N. R., Devendram, V., Pal, M., and Iqbal, J. Finally, authors succeeded by reacting matrine 72) with diphenyl disulfide in the presence of LDA to obtain 14-thio phenyl matrine 74) in 96% yield followed by IBX oxidation in acidic aqueous solution in 95% yield. Bizzarri B. M., Botta L., Capecchi E., Celestino I., Checconi P., Palamara A. T., et al. IBX DMSO, THF, 2 h, 20 C 65% HO HO OPMB OTBDPS O OTBDPS Ref. Studies were also conducted to select a better solvent for which water, methanol, ethanol, chloroform, dichloromethane, DMF, acetonitrile, THF, and DMSO were examined. IBX, 2-Iodoxybenzoic acid - Organic Chemistry Portal Authors proposed that the reaction proceeded through the intermediary of an aryl radical generated through the oxidation of the aryl hydrazine 9) molecule by IBX. MeSH A mechanism was proposed for the IBX-supported cyclo-desulfurization of acylthiosemicarbazides. Hypervalent Iodine Reactions Utilized in Carbon-Carbon Bond Formations. Zhang Z., Song X., Li G., Li X., Zheng D., Zhao X., et al. It involves catalyst-free nucleophilic addition of amines 2) on benzoxazoles (107) under solvent-free conditions, followed by IBX-assisted oxidative ring closure. Epub 2015 Dec 9. Tetrahedron Lett. Other oxidants, with the exception of IBX, resulted in lower yields of the desired products. One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels-Alder Cycloaddition. Authors explained the mechanism of this interesting and important cascade reaction. (2013). (2016). Mironov VF, Nemtarev AV, Tsepaeva OV, Dimukhametov MN, Litvinov IA, Voloshina AD, Pashirova TN, Titov EA, Lyubina AP, Amerhanova SK, Gubaidullin AT, Islamov DR. Molecules. The present review highlights research reports on IBX-assisted transformations in heterocyclic derivatives, particularly from 2010 onward. The PubMed wordmark and PubMed logo are registered trademarks of the U.S. Department of Health and Human Services (HHS). doi:10.1021/acs.orglett.9b00047, Yoshimura, A., and Zhdankin, V. V. (2016). Pravin Patil et al. Biomol. The authors of this review acknowledge the original contributors and publishers of the articles cited here. Organic Chemistry Laboratory, Foreign Visiting Professor, School of Chemistry and Food, Federal University of Rio Grande-FURG, Rio Grande, Brazil, 3 cookies. 10:841751. doi: 10.3389/fchem.2022.841751. 52, 21282131. Catalytic use of o-iodoxybenzoic acid (IBX) in the presence of Oxone as a co-oxidant is demonstrated for the oxidation of primary and secondary alcohols in user- and eco-friendly solvent mixtures.Also demonstrated is the in situ (re)oxidation of 2-iodosobenzoic acid (IBA) and even commercially available 2-iodobenzoic acid (2IBAcid) by Oxone to IBX allowing one to use these less hazardous . Initially, authors examined the effect of solvents such as DMF, CH3CN, and DMSO and oxidants such as K2S2O8, oxone, and IBX. In the initial studies, authors screened several catalysts such as TBHS, -CD, CuCl, CAS, iodine, DABCO, and DHP apart from IBX for their efficacy and observed that IBX afforded the best results for the reaction. Authors examined the efficacy of KIO3, KIO4, HIO4, H2O2, O2, and IBX for the oxidative ring-closure step. The method was applied by the authors in the four-step total synthesis of the marine alkaloid eudistomin U (115), with an indole skeleton 113) (Supplementary Figure S42). Silva T. S., Zeoly L. A., Coelho F. (2020). Kamlesh Kumar et al. By continuing you agree to the A broad range of propargyl vinyl ethers 3) was used effectively. 54, 44834486. An efficient and practical system for the catalytic oxidation of alcohols, aldehydes, and alpha,beta-unsaturated carboxylic acids. The reaction starts by a substitution on the iodine where the . The Mannich precursors were subjected to intramolecular oxidative annulation in DMA at 80C in good to excellent yields affording imidazo [1,2-a] fused bicyclic scaffolds promoted by the oxidant IBX and additive NIS. 2020 official website and that any information you provide is encrypted Thus, we established a highly efficient and selective method for the oxidation of primary and secondary alcohols to carbonyl compounds such as aldehydes, carboxylic acids, . Among solvents, DMSO was proved to be useful. 79, 23312336. Substrate scope was studied using several substituted phenylhydrazines 9), and 2-substituted naphthoquinones 8) were used. (2019). Chaojie Li and co-authors in an interesting research communication described a metal-free, eco-friendly, and operationally simple approach for the semisynthesis of sophocarpine 73) from matrine 72) in 91% yield, via the formation of 14-phenyl sulfinyl matrine 74) with efficient and controllable oxidation of thioether 74) to sulfoxide 75) by IBX/H2O as the key step (Supplementary Figures S28,S29) (Li et al., 2014). 139, 43544357. 47, 11101120. Tetrahedron Lett. doi:10.1016/j.tetlet.2013.12.060, Li, Y., Hari, D. P., Vita, M. V., and Waser, J. Initially, TMS-protected trifluoromethylated alcohols were obtained from the respective aldehydes 22) by reacting with TMSCF3 79) in the presence of the catalytic amount of K2CO3 in DMF at room temperature. A broad range of propargyl vinyl ethers 3) was used effectively. IBX-TfOH Mediated Oxidation of Alcohols to Aldehydes and Ketones under Mild Reaction Conditions, Controllable and Efficient Oxidation of Thioether by 2-iodoxybenzoic Acid (IBX) in Water: Semisynthesis of Sophocarpine. *Correspondence: Yadavalli Venkata Durga Nageswar, dryvdnageswar@gmail.com, Metal-Free Oxidative Transformations in Organic Synthesis, View all Tetrahedron 66, 60476053. 2-Iodoxybenzoic acid - Wikipedia heat-sensitive,25,26 at least under certain conditions, thus weakening its routine for large-scale applications. One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels-Alder Cycloaddition. Commun. N-protecting groups were well tolerated. Sci. The Mechanism of Dess-Martin Oxidation. Brown LE, Landaverry YR, Davies JR, Milinkevich KA, Ast S, Carlson JS, Oliver AG, Konopelski JP. Wagh Y. S., Tiwari N. J., Bhanage B. M. (2013). (2019). During study, authors examined the feasibility of several bases and solvents such as NaH/THF, NaH/PhCH3, LDA/THF, and LiHMDS/THF for the direct sulfinylation of matrine 72) using methyl phenyl sulfinate with little or no desired product formation. The protocol covered a variety of acyl hydrazides (9b) and isothiocyanates (105). Concise total synthesis of ()-actinophyllic acid. IBX is prepared from 2-iodobenzoic acid, potassium bromate, and sulfuric acid. In the last stage of the process, 5-exo-dig-hetero cyclization was facilitated by (Ph3P) AuCl (5mol%) at 38C. Nishanth Verma and co-authors employed LiBr/-CD in the H2ODMSO mixture for highly regioselective ring cleavage of epoxides 12) affording bromohydrins 13) (Supplementary Figure S6). DFT-Based Comparison between Mechanistic Aspects of Amine and Alcohol Oxidation Mediated by IBX. The reaction tolerates a wide variety of functional groups. 61, 151749151754. Hypervalent Iodine(V) Mediated Mild and Convenient Synthesis of Substituted 2-Amino-1,3,4-Oxadiazoles. sharing sensitive information, make sure youre on a federal In the one-pot two-step aza-FriedelCrafts reaction, 2-substituted pyrrolidines 27) were obtained from suitable nucleophiles in the presence of TFA, in modest to good yields and high to excellent diastereoselectivity. A simple method for the oxidation of primary alcohols with o Other oxidants, with the exception of IBX, resulted in lower yields of the desired products. Primary alcohols can be oxidized to either aldehydes or carboxylic acids depending on the reaction conditions. (2018). All the primary alcohols 71) were oxidized to aldehydes 22) in good yields (9097%). Authors also successfully examined the efficiency and selectivity of recyclable IBX-polystyrene toward the dehydrogenation reaction of methoxylated flavanones 86). -proline analogs (110) in the aqueous medium assisted by the supramolecular host -CD under room temperature conditions (Supplementary Figures S39,S40) (Murthy and Nageswar, 2011). Authors assessed the efficacy of different commercially available hypervalent iodine reagents, such as (diacetoxy) iodobenzene (PIDA), DessMartin periodinane (DMP), [bis(trifluroacetoxy)]iodo benzene (PIFA), and o-iodoxybenzoic acid (IBX). 50, 58205822. The present review highlights research reports on IBX-assisted transformations in heterocyclic derivatives, particularly from 2010 onward. Tetrahedron Lett. ()-Camphor Sulfonic Acid Assisted IBX Based Oxidation of 1 and 2 Alcohols. S. Silva and co-authors by a fast, mild, atom-efficient protocol involving sequential one-pot IBX oxidation of MoritaBaylisHillman (MBH) adducts and catalyst-free conjugate addition of indolizine derivatives 65) as nucleophiles (Supplementary Figure S24) (Silva et al., 2020). During the optimization studies, different solvents and stoichiometric ratios are examined. Several antioxidants and anti-influenza moieties containing pyrogallol 44) and catechol structures were made by Bruno. Synth. A plausible mechanism for the acid-catalyzed oxidation of alcohols with IBX was explained. The https:// ensures that you are connecting to the Org Lett. 21, 19891993. also thanks the CNPq-TWAS fellowship., The Supplementary Material for this article can be found online at: https://www.frontiersin.org/articles/10.3389/fchem.2022.841751/full#supplementary-material, Banik, S. M., Mennie, K. M., and Jacobsen, E. N. (2017). Org. IBX (2iodoxybenzoic acid), discovered in 1893, is an oxidant in synthetic chemistry whose Accepted 00th January 2012 DOI: 10.1039/x0xx00000x extensive use is impeded by its explosiveness at high temperature and poor solubility in common organic solvents except DMSO. doi:10.1021/jo500131h, Prabhu, G., and Sureshbabu, V. V. (2012). The reactions carried out under solvent-free conditions and water medium provided better results. The protocol includes a proline-catalyzed direct Mannich reactioncyclization sequence between the in situ-generated aryl/heteroaryl/indolyl-imines and succinaldehyde (29). Biomol. (2014). 2-Iodoxybenzoic acid ( IBX) is an organic compound used in organic synthesis as an oxidizing agent. LiBr/-CD/IBX/H2O-DMSO: A New Approach for One-Pot Biomimetic Regioselective Ring Opening of Chalcone Epoxides to Bromohydrins and Conversion to 1,2,3-triketones. In the second step, these intermediary compounds undergo condensation with aryl/heteroaryl amines 2) followed by cyclization resulting in the highly substituted pyrrole derivatives 1) in the CH2Cl2 medium. Li Y., Hari D. P., Vita M. V., Waser J. Organic Catalysis and Biocatalysis Laboratory-LACOB, Federal University of Grande Dourados-UFGD, Dourados, Brazil, Samata Shetgaonkar, VIT University, India. 2021 Oct 20;26(21):6350. doi: 10.3390/molecules26216350. 2.0 M H2SO4 65 C, 2.5 h + + 85 C . 114, 92199280. Free Radic Biol Med. doi:10.1021/jacs.7b01443, Murthy, S. N., and Nageswar, Y. V. D. (2011). These bromohydrins 13) were later converted successfully into 1, 2, 3-triketones 14) by the IBX-mediated oxidation in DMSO under room temperature conditions (Verma et al., 2017). J Org Chem. Accessibility unveiled that IBX promoted mild and selective oxidation of unactivated cyclic amines (2b) to imines (25), employing a range of aliphatic meso-pyrrolidines (2b) as substrates (Supplementary Figure S10) (de Graaff et al., 2015) The protocol was further applied for diastereoselective oxidative Ugi-type and aza-FriedelCrafts reactions (26, 27) (Supplementary Figures S11,S12). Researchers are advised to refer original articles for any detailed information. The site is secure. Chem. The protocol was efficiently applied for generating diverse bioactive fused heterocyclic scaffolds such as pyrrolo-oxadiazole, dihydro pyrrolo-quinoline, pyrrolo-quinoline, and pyrrolophenanthridine. Heterocyclic compounds widely occur in nature and play a significant role in human life. Authors also investigated on relative nucleophilicity of indolizines/indoles 67) and concluded that the indolizine skeleton 67) appeared to be a superior nucleophile in the present reaction conditions. An official website of the United States government. Singh A., Mir N. A., Choudhary S., Singh D., Sharma P., Kant R., et al. The methodology was extended to prepare some arylbenzoxazoles containing amino acids 69). Finally, authors succeeded by reacting matrine 72) with diphenyl disulfide in the presence of LDA to obtain 14-thio phenyl matrine 74) in 96% yield followed by IBX oxidation in acidic aqueous solution in 95% yield. Authors explained the reaction mechanism. Org. Authors claim that the high solubility of IBX in DMSO and its ability to dehydrogenase carbonyl functionality with the corresponding , -unsaturated moieties made this protocol feasible. This high-yielding approach involves IBX-promoted oxidation of secondary amine (2b) followed by isonitrile--addition and aza-DielsAlder cycloaddition. Stereocontrolled synthesis of resolvin D1. described an efficient scalable and practical method for the IBXTfOH-assisted oxidation of primary and secondary alcohols 77) in 1,4-dioxane at ambient temperature to afford aldehydes 22) and ketones (103) in quantitative yields (Supplementary Figure S36) (Kumar et al., 2020). Hypervalent Iodine: a Powerful Electrophile for Asymmetric -functionalization of Carbonyl Compounds. Recent Advances in Intramolecular Metal-free Oxidative C-H Bond Aminations Using Hypervalent Iodine(III) Reagents. After initial studies, authors observed that the reaction proceeded well in the presence of 1.2 eq. Highly Efficient Synthesis of Aryl and Heteroaryl Trifluoromethyl Ketones via O-Iodobenzoic Acid (IBX). Creative Commons Attribution License (CC BY). The https:// ensures that you are connecting to the Chem. Willgerodt, C. (1886). Highly functionalized indolizine scaffolds 64) were produced by Thiago. (2018). It was observed that DMP and HIO3 afforded 67 and 56%, respectively, when 2-amino-1,4-naphthoquinone was used as a standard material, whereas IBX gave 78% of the desired product. 8, 1544815458. Synthesis of Spirooxindoles from N-Arylamide Derivatives via Oxidative C(sp2)-C(sp3) Bond Formation Mediated by PhI(OMe)2 Generated In Situ. developed direct oxidative arylation of naphthoquinones 8) employing o-iodoxybenzoic acid and aryl hydrazines 9) in acetonitrile at room temperature (Supplementary Figures S4,S5) (Patil et al., 2014). and transmitted securely. Keywords: (2011). Retired Chief Scientist, Indian Institute of Chemical Technology-IICT, Hyderabad, India, 2 The protocol covers a broad range of . The protocol covered a variety of acyl hydrazides (9b) and isothiocyanates (105). Bethesda, MD 20894, Web Policies This site needs JavaScript to work properly. Careers. THF, CHCl3, toluene, ACN, and DMSO were tried as solvents, and out of these ACN was found to be ideal. The present review highlights research reports on IBX-assisted transformations in heterocyclic derivatives, particularly from 2010 onward. The role of the CSA/IBX catalytic system in the reaction was presented mechanistically. Xing, L., Zhang, Y., Li, B., and Du, Y. Citation numbers are available from Dimensions, Department of Chemistry, School of Advanced Sciences, VIT University, India, Indian Institute of Technology Roorkee, India. A mild room temperature oxidative dimerization of thioamides 116) under the influence of the IBX/TEAB system in acetonitrile solvent to afford 3,5-disubstituted-1,2,4-thiadiazoles 117) in high yields was described by (Supplementary Figure S43) Patil et al. The protocol covers a broad range of substrates with alkene, arene, and heteroarene functionalities. C. de Graaff et al. Ozanne A, Pouysgu L, Depernet D, Franois B, Quideau S. Org Lett. All the figures are redrawn to give an idea about the research work discussed in the text. Books, Contact and When solvents such as DCM, DCE, ACN, and EtOAc are used, the reactions may need higher temperatures. The reaction mechanism for the product formations was explained appropriately. Chem. Authors examined the efficiency of IBX in the oxidation of a series of flavanones 84) and flavones 90). Chem. The site is secure. The stoichiometry of IBX and TEA was fixed after studies. N-protecting groups were well tolerated. ABAB Phthalocyanines: Scaffolds for Building Unprecedented Donor--Acceptor Chromophores. 49, 79267928. Tetrahedron Lett. Authors successfully employed various aliphatic and aromatic isocyanides and electronically diverse carboxylic acids as compatible reactions in the Ugi-type reactions. Would you like email updates of new search results? A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate ,-diolcarbonate aldehyde to (E)--hydroxy-,-enal has been developed. Computational exploration of copper catalyzed vinylogous aerobic oxidation of unsaturated compounds. described the synthesis of highly functionalized pyridines 15) by a one-pot metal-free domino approach (Gade et al., 2013). Chem. In an interesting research article submitted by Jorg. Epub 2017 Feb 10. Cheng H., Pei Y., Leng F., Li J., Liang A., Zou D., et al. These bromohydrins 13) were later converted successfully into 1, 2, 3-triketones 14) by the IBX-mediated oxidation in DMSO under room temperature conditions (Verma et al., 2017). A large library of aryl/heteroaryl trifluoromethyl alcohols 77) and aryl/heteroaryl trifluromethyl ketones 78) was prepared by Huicheng Cheng and co-authors from the corresponding aldehydes 22) in excellent yields (Supplementary Figures S30,S31) (Cheng et al., 2013). The .gov means its official. (2017). The aliphatic and heteroaromatic substituents at C 1) also did not hinder the reaction. Authors observed that the substitution on the quinoline ring strongly influenced the reaction. ScienceDirect is a registered trademark of Elsevier B.V. Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation.
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