Study on the reactive transient α-λ3-iodanyl- acetophenone complex in the iodine(III)/PhI(I) catalytic cycle of iodobenzene-catalyzed α-acetoxylation reaction of acetophenone by electrospray ionization tandem mass spectrometry

Rapid Communications in Mass Spectrometry

Volumn 26, Issue 6, 2012, Pages 616-620

  Wang, Hao Yang ^a   Zhou, Juan ^a   Guo, Yin Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYTIC OXIDATION; ELECTROSPRAY IONIZATION; IONIZATION OF GASES; KETONES; MASS SPECTROMETRY; PH; REACTION INTERMEDIATES;

ACETOPHENONES; ACETOXYLATION; CATALYTIC CYCLES; ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY; ESI-MS-MS; HYPERVALENT IODINE COMPOUNDS; IODINE SPECIES; IODOBENZENE; M-CHLOROPERBENZOIC ACID; REACTION SOLUTIONS;

ACETIC ACID;

EID: 84863134373     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6145     Document Type: Article

References (28)

1. Y. H. Yang, F. Diederich, J. S. Valentine,. Lewis acidic catalysts for olefin epoxidation by iodosylbenzene. J. Am. Chem. Soc. 1991, 113, 7195.
2. P. J. Stang, V. V. Zhdankin,. Organic polyvalent iodine compounds. Chem. Rev. 1996, 96, 1123.
3. E. D. Matveeva, M. V. Proskurnina, N. S. Zefirov,. Polyvalent iodine in organic chemistry: Recent developments, 2002-2005. Heteroatom Chem. 2006, 17, 595.
4. V. V. Zhdankin, P. J. Stang,. Chemistry of polyvalent iodine. Chem. Rev. 2008, 108, 5299.
5. T. Dohi,. Development of environmentally benign oxidations using hypervalent iodine (III) reagents. Yakugaku Zasshi-J. Pharm. Soc. Jpn. 2006, 126, 757.
6. T. Dohi, Y. Kita,. Hypervalent iodine reagents as a new entrance to organocatalysts. Chem. Commun. 2009, 2073.
7. A. Varvoglis,. Polyvalent iodine compounds in organic synthesis. Synthesis 1984, 709.
8. L. F. Silva Jr., Hypervalent iodine-mediated ring contraction reactions. Molecules 2006, 11, 421.
9. Z. Li, Z. H. Tang, X. X. Hu, C. G. Xia,. Insight into the mechanism of oxidative kinetic resolution of racemic secondary alcohols by using manganese(III) (salen) complexes as catalysts. Chem. Eur. J. 2005, 11, 1210.
10. J. W. Sam, X. J. Tang, R. S. Magliozzo, J. Peisach,. Electrospray mass spectrometry of iron bleomycin II: Investigation of the reaction of Fe(III)-bleomycin with iodosylbenzene. J. Am. Chem. Soc. 1995, 117, 1012.
11. H. W. Richter, B. R. Cherry, T. D. Zook, G. F. Koser,. Characterization of species present in aqueous solutions of [hydroxy(mesyloxy)iodo]benzene and [hydroxy(tosyloxy)iodo]benzene. J. Am. Chem. Soc. 1997, 119, 9614.
12. L. F. Silva Jr, N. P. Lopes,. A study on the species present in solutions of hypervalent iodine(III) reagents by electrospray ionization mass spectrometry. Tetrahedron Lett. 2005, 46, 6023.
13. L. F. Silva Jr, R. S. Vasconcelos, N. P. Lopes,. Application of high-resolution electrospray mass spectrometry for the elucidation of the disproportionation reaction of iodobenzene diacetate. Int. J. Mass Spectrom. 2008, 276, 24.
14. R. D. Richardson, T. Wirth,. Hypervalent iodine goes catalytic. Angew. Chem. Int. Ed. 2006, 45, 4402.
15. V. V. Zhdankin,. Hypervalent iodine(III) reagents in organic synthesis. Arkivoc 2009, i, 1.
16. T. Wirth,. Hypervalent iodine chemistry in synthesis: Scope and new directions. Angew. Chem. Int. Ed. 2005, 44, 3656.
17. T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, M. Shiro, Y. Kita,. A unique site-selective reaction of ketones with new recyclable hypervalent iodine (III) reagents based on a tetraphenylmethane structure. Chem. Commun. 2005, 2205.
18. C. L. Hill,. Homogeneous catalysis-controlled green oxidation. Nature 1999, 401, 436.
19. M. Ochiai, Y. Takeuchi, T. Katayama, T. Sueda, K. Miyamoto,. Iodobenzene-catalyzed alpha-acetoxylation of ketones. In situ generation of hypervalent (diacyloxyiodo)benzenes using m-chloroperbenzoic acid. J. Am. Chem. Soc. 2005, 127, 12244.
20. T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, Y. Kita,. Versatile hypervalent-iodine(III)-catalyzed oxidations with m-chloroperbenzoic acid as a cooxidant. Angew. Chem. Int. Ed. 2005, 44, 6193.
21. M. N. Eberlin,. Electrospray ionization mass spectrometry: a major tool to investigate reaction mechanisms in both solution and the gas phase. Eur. J. Mass Spectrom. 2007, 13, 19.
22. L. S. Santos,. Online mechanistic investigations of catalyzed reactions by electrospray ionization mass spectrometry: A tool to intercept transient species in solution. Eur. J. Org. Chem. 2008, 2, 235.
23. L. S. Santos,. Reactive Intermediates: MS Investigations in Solution. Wiley-VCH, Weinheim, 2010.
24. H. Y. Wang, J. O. Metzger,. ESI-MS study on first-generation ruthenium olefin metathesis catalysts in solution: Direct detection of the catalytically active 14-electron ruthenium intermediate. Organometallics 2008, 27, 2761.
25. H. Y. Wang, W. L. Yim, T. Klüner, J. O. Metzger,. ESIMS studies and calculations on alkali-metal adduct ions of ruthenium olefin metathesis catalysts and their catalytic activity in metathesis reactions. Chem. Eur. J. 2009, 15, 10948.
26. Z. X. Zhao, H. Y. Wang, Y. L. Guo,. ESI-MS study on transient intermediates in the fast cyclopropenium-activated chlorination reaction of alcohols. J. Mass Spectrom. 2011, 46, 856.
27. H. Tohma, S. Takizawa, T. Maegawa, Y. Kita,. Facile and clean oxidation of alcohols in water using hypervalent iodine(III) reagents. Angew. Chem. Int. Ed. 2000, 39, 1306.
28. H. Tohma, Y. Kita,. Hypervalent iodine reagents for the oxidation of alcohols and their application to complex molecule synthesis. Adv. Synth. Catal. 2004, 346, 111.