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Sodium Percarbonate: a Versatile Oxidizing Reagent

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Sodium Percarbonate: a Versatile Oxidizing Reagent SPOTLIGHT 2969 SYNLETT Sodium Percarbonate: A Versatile Spotlight 335 Oxidizing Reagent Compiled by Nadiya Koukabi This feature focuses on a re- Nadiya Koukabi was born in Shiraz, Iran. She received her B.Sc. agent chosen by a postgradu- (2000) in Chemistry from the Islamic Azad University Firouzabad ate, highlighting the uses and Branch and her M.Sc. in Organic Chemistry from the Bu-Ali Sina preparation of the reagent in University under the guidance of Prof. M. A. Zolfigol. She is pres- current research ently working toward her Ph.D. degree under the supervision of Prof. A. Khazaei and Prof. M. A. Zolfigol. Her research interests fo- cuse on the development of new reagents and catalysts in organic reactions. Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran E-mail: [email protected] Introduction available and furthermore, it is more risky to handle. Con- sequently, the ability of SPC to release oxidative species Sodium percarbonate (SPC, Na2CO3·1.5H2O) is an inor- in an organic medium has made it an useful reagent in or- ganic, inexpensive, environmentally friendly, stable, and ganic synthesis.8–11 easily handled reagent that has an excellent shelf life. The + Na H H H H – O O O O O name ‘sodium percarbonate’ does not reflect the structure O + O Na H O O or true nature of the material. Its erroneous name is due to + O Na – H H O 1,2 H successive confusions in its structure. The structure of – O O + H Na + Na – SPC (Figure 1) has been determined, the cohesion of the – O O O O O H – + O Na adduct being due to hydrogen bonding between carbonate O – – – O O 3,4 O O + ions and hydrogen peroxide molecules. Therefore, a Na H H H – O – O O O O more judicious appellation of SPC is ‘sodium carbonate + O O O Na + H 5 H Na O + peroxyhydrate’. The structure of SPC has led it to be con- + Na – Na H sidered as a solid form,6or dry carrier of hydrogen perox- O ide. Figure 1 Structure of sodium percarbonate SPC is relatively soluble in water (at 20 °C, 140 g/L) and 7 Na CO 1.5H O 1.5H O CO Na ⋅ 2 3 2 2 the pH of 1% aqueous solution of it is ca. 10.5. The hy- + 2 2 3 drogen peroxide present in SPC is spontaneously released 2 in water. Concentrated hydrogen peroxide is not readily Scheme 1 Preparation of sodium percarbonate12 Abstracts (A) Oxidation of Pyridines to the Corresponding N-Oxides: A combination of Tf2O and Na2CO3·1.5H2O has been developed for Tf O, SPC 13 2 the oxidation of highly electron-deficient pyridines. The N-oxida- + MeCN, 0 °C Cl Cl N Cl Cl tion reaction, utilizing in situ generated peracid, proceeds under mild N – conditions that allow for the presence of acid-sensitive functional O groups. (B) Asymmetric Epoxidation of a,b-Unsaturated Ketones: O This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. O ( -Leu)nAMPSi SPC acts as an efficient oxidant in the epoxidation of (E)-a,b-unsat- L O 1 2 1 2 R L R R urated aromatic ketones with silica-grafted poly-( )-leucine as a R chiral catalyst to yield optically active epoxy ketones in high enantio- SPC 14 ( -Leu)@AMPSi: silica-grafted poly-( )-leucine L selectivities (up to 93% ee). L SYNLETT 2010, No. 19, pp 2969–2970 xx.xx.2010 Advanced online publication: 03.11.2010 DOI: 10.1055/s-0030-1258997; Art ID: V34010ST © Georg Thieme Verlag Stuttgart · New York 2970 SPOTLIGHT (C) Iodination of Arenes: AcOH, Ac O, H SO 2 2 4 An eco-friendly and easy laboratory procedures for oxidative iodina- ArH ArI , SPC, 45–50 °C 15 I tion of various arenes is achieved with SPC as oxidant. 2 (D) Preparation of Aromatic Carboxylic Acids: Bjørsvik and co-workers16 oxidized methyl aryl ketones with O Me O OH Na2CO3·1.5H2O or NaBO3·4H2O in the presence of a catalytic 1 t-BuOH (12 ml) R R1 amount of nitroarenes to provide the corresponding aromatic carbox- 1,3-(O2N)2C6H4 (10 mol%) ylic acids in good yields without production of any harmful side 4 2 t-BuOK, SPC products. The method shows excellent selectivity when the model R R 80 °C, 5 h R4 R2 3 substrate (acetophenone) is oxidized. R R3 Epoxidation of a,b-Unsaturated Aldehydes: (E) Direct asymmetric O O O SPC, CHCl , r.t. epoxidation of a,b-unsaturated aldehydes with peroxides or SPC in 3 H O 2 EtO C H C H EtO the presence of organocatalyst is presented. In particular, protected 2 2 Ph a,a-diphenyl-2-prolinol catalyzed the asymmetric epoxidation with (cat.) Ph N excellent stereoselectivity and furnished the desired products in high C efficiency with up to 96:4 dr and 98% ee.17 H OTMS (F) Preparation of Ketones: Highly efficient and selective oxidations of alcohols to ketones un- SPC or SPB, 1 der organic-solvent-free and transition-metal-free conditions have 1 R R H been developed with sodium percarbonate as an oxidant. For a range aq HBr (20 mol%) O AcOH, 50 °C 2 of activated and non-activated alcohols the selective oxidation of OH 2 R secondary alcohols in the presence of primary alcoholic and other R functional groups have been described.18 (G) Synthesis of Sulfoxides: Gomez and co-workers have demonstrated that SPC can be used for the electrophilic oxidation of sulfides under solvent-free conditions. O O O SPC or SPB S S A comparative study concerning the effect of the oxidant and reac- S 1 2 1 2 1 2 R R R R R tion conditions on yield and chemoselectivity (sulfoxide vs. sulfone) R has been carried out.19 (H) Homocoupling: SPC, CuI, PdCl 2 C CH R C C R SPC could be used both as a clean oxidant and as base in aqueous RC O PPh (cat.) 2 O media for the Pd/Cu co-catalyzed homocoupling of terminal Pol alkynes.20 H O–MeCN, 25 °C 2 References (1) Carpeni, G. Bull. Soc. Chim. Fr. 1949, 742. (11) Zhao, G.-L.; Ibrahem, I.; Sunden, H.; Cordova, A. Adv. (2) Partington, J. R.; Fathallah, A. H. J. Chem. Soc. 1950, 1934. Synth. Catal. 2007, 349, 1210. (3) Carrondo, M. A. A. F. d. e. C. T.; Griffith, W. P.; Jones, D. (12) Ruiz, E. J.; Ortega-Borges, R.; Jurado, J. L.; Chapman, T. P.; Skapski, A. C. J. Chem. Soc., Dalton Trans. 1977, 2323. W.; Meas, Y. Electrochem. Solid-State Lett. 2009, 12, E1. (4) Adams, J. M.; Pritchard, R. G. Acta Crystallogr. Sect. B (13) Zhu, X.; Kreutter, K. D.; Hu, H.; Player, M. R.; Gaul, M. D. 1977, 33, 3650. Tetrahedron Lett. 2008, 49, 832. (5) Zhubrikov, A. V.; Legurova, E. A.; Gutkin, V.; Uvarov, V.; (14) Yi, H.; Zou, G.; Li, Q.; Chen, Q.; Tang, J.; He, M. Y. This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. Khitrov, N. V.; Lev, O.; Tripol’skaya, T. A.; Prikhodchenko, Tetrahedron Lett. 2005, 46, 5665. P. V. Russ. J. Inorg. Chem. 2009, 54, 1455. (15) Zielinska, A.; Skulski, L. Molecules 2005, 10, 1307. (6) Khanmohammadi, M.; Kargosha, K. Talanta 2005, 65, 824. (16) Bjørsvik, H. R.; Merinero, J. A. V.; Liguori, L. Tetrahedron (7) OECD SIDS Initial Assessment Report, for SIAM 20 (CAS Lett. 2004, 45, 8615. N: 15630-89-4), 2005; Sponsor Country: Poland; (17) Sunden, H.; Ibrahem, I.; Cordova, A. Tetrahedron Lett. http://www.heraproject.com. 2006, 47, 99. (8) Habibi, D.; Zolfigol, M. A.; Safaiee, M.; Shamsian, A.; (18) Suman, L. J.; Vishal, B. S.; Bir, S. Tetrahedron 2006, 62, Ghorbani-Choghamarani, A. Catal. Commun. 2009, 10, 6841. 1257. (19) Gomez, M. V.; Caballero, R.; Vazquez, E.; Moreno, A.; (9) Jain, S. L.; Joseph, J. K.; Sain, B. Synlett 2006, 2661. Hoz, A.; Daz-Ortiz, A. Green Chem. 2007, 9, 331. (10) Kjonaas, R. A.; Clemons, A. E. J. Chem. Educ. 2008, 85, (20) Zhou, L.; Zhan, H. Y.; Liu, H. L.; Jiang, H. F. Chin. J. Chem. 827. 2007, 25, 1413. Synlett 2010, No. 19, 2969–2970 © Thieme Stuttgart · New York.
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