Heck coupling in the gas phase: Examination of the reaction mechanism by ion/molecule reactions and mass spectrometry

International Journal of Mass Spectrometry

Volumn 308, Issue 2-3, 2011, Pages 307-310

  Fiebig, Lukas ^a   Schmalz, Hans Günther ^a   Schäfer, Mathias ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Accurate ion mass measurements; Charge tag substrates; Gas phase Heck reaction; Ion molecule reactions; Reaction mechanism; Tandem mass spectrometry

Indexed keywords

EID: 80955158423     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2011.07.013     Document Type: Article

References (33)

1. M. Beller, and C. Bolm Transition Metals for Organic Synthesis 2004 Wiley-VCH Weinheim
2. R.F. Heck Palladium-catalyzed reactions of organic halides with olefins Acc. Chem. Res. 12 1979 146 151
3. The Mizoroki-Heck Reaction 2009 John Wiley & Sons Ltd. West Sussex, United Kingdom
4. E.I. Negishi, and A. de Meijere Handbook of Organopalladium Chemistry for Organic Synthesis 2002 John Wiley & Sons, Inc. New York
5. I.P. Beletskaya, and A.V. Cheprakov The heck reaction as a sharpening stone of palladium catalysis Chem. Rev. 100 2000 3009 3066
6. E.I. Negishi, C. Coperet, S.M. Ma, S.Y. Liou, and F. Liu Cyclic carbopalladation. A versatile synthetic methodology for the construction of cyclic organic compounds Chem. Rev. 96 1996 365 393 (Pubitemid 126637725)
7. X.F. Wu, P. Anbarasan, H. Neumann, and M. Beller From noble metal to nobel prize: palladium-catalyzed coupling reactions as key methods in organic synthesis Angew. Chem. Int. Ed. 49 2010 9047 9050
8. J.P. Knowles, and A. Whiting The Heck-Mizoroki cross-coupling reaction: a mechanistic perspective Org. Biomol. Chem. 5 2007 31 44 (Pubitemid 44927097)
9. J.B. Fenn, M. Mann, C.K. Meng, S.F. Wong, and C.M. Whitehouse Electrospray ionization for mass-spectrometry of large biomolecules Science 246 1989 64 71 (Pubitemid 19252085)
10. R. Cole Electrospray Ionization Mass Spectrometry: Fundamentals, Instrumentation and Applications 1997 John Wiley & Sons New York
11. P. Kebarle, and U.H. Verkerk Electrospray: from ions in solution to ions in the gas phase, what we know now Mass Spectrom. Rev. 28 2009 898 917
12. J.M. Wells, and S.A. McLuckey The Encyclopedia of Mass Spectrometry 2003 Elsevier New York
13. 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. 13 2007 19 28
14. A.A. Sabino, A.H.L. Machado, C.R.D. Correia, and M.N. Eberlin Probing the mechanism of the Heck reaction with arene diazonium salts by electrospray mass and tandem mass spectrometry Angew. Chem. Int. Ed. 43 2004 2514 2518 (Pubitemid 39257712)
15. L.S. Santos, C.H. Pavam, W.P. Almeida, F. Coelho, and M.N. Eberlin Probing the mechanism of the Baylis-Hillman reaction by electrospray ionization mass and tandem mass spectrometry Angew. Chem. Int. Ed. 43 2004 4330 4333 (Pubitemid 39257412)
16. L.S. Santos, and J.O. Metzger Study of homogeneously catalyzed Ziegler-Natta polymerization of ethene by ESI-MS Angew. Chem. Int. Ed. 2006 977 981 (Pubitemid 43198490)
17. P. Chen Electrospray ionization tandem mass spectrometry in high-throughput screening of homogeneous catalysts Angew. Chem. Int. Ed. 42 2003 2832 2847 (Pubitemid 36880799)
18. C.D. Buarque, V.D. Pinho, B.G. Vaz, M.N. Eberlin, A.J.M. da Silva, and P.R.R. Costa Palladium-catalyzed oxyarylation of olefins using silver carbonate as the base. probing the mechanism by electrospray ionization mass spectrometry J. Org. Chem. 695 2010 2062 2067
19. T.D. Fernandes, B.G. Vaz, M.N. Eberlin, A.J.M. da Silva, and P.R.R. Costa Palladium-catalyzed tandem Heck-lactonization from o-iodophenols and enoates: synthesis of Coumarins and the study of the mechanism by electrospray ionization mass spectrometry J. Org. Chem. 75 2010 7085 7091
20. L.S. Santos, L. Knaack, and J.O. Metzger Investigation of chemical reactions in solution using API-MS Int. J. Mass Spectrom. 246 2005 84 104 (Pubitemid 41455397)
21. K.L. Vikse, M.A. Henderson, A.G. Oliver, and J.S. McIndoe Direct observation of key intermediates by negative-ion electrospray ionisation mass spectrometry in palladium-catalysed cross-coupling Chem. Commun. 46 2010 7412 7414
22. L.S. Santos, G.B. Rosso, R.A. Pilli, and M.N. Eberlin The mechanism of the stille reaction investigated by electrospray ionization mass spectrometry J. Org. Chem. 72 2007 5809 5812 (Pubitemid 47104687)
23. F. Coelho, and M.N. Eberlin Angew. Chem. Int. Ed. 50 2011 5261 5263
24. R. Colton, and J.C. Traeger The Application of electrospray mass-spectrometry to ionic inorganic and organometallic systems Inorg. Chim. Acta 201 1992 153 155
25. C. Hinderling, C. Adlhart, and P. Chen Olefin metathesis of a ruthenium carbene complex by electrospray ionization in the gas phase Angew. Chem. Int. Ed. 37 1998 2685 2689 (Pubitemid 28501523)
26. C. Adlhart, C. Hinderling, H. Baumann, and P. Chen Mechanistic studies of olefin metathesis by ruthenium carbene complexes using electrospray ionization tandem mass spectrometry J. Am. Chem. Soc. 122 2000 8204 8214
27. J.S. McIndoe, and D.M. Chisholm Charged ligands for catalyst immobilisation and analysis Dalton Trans. 2008 3933 3945
28. M.A. Schade, J.E. Feckenstein, P. Knochel, and K. Koszinowski Charged tags as probes for analyzing organometallic intermediates and monitoring cross-coupling reactions by electrospray-ionization mass spectrometry J. Org. Chem. 75 2010 6848 6857
29. A. Makarov Electrostatic axially harmonic orbital trapping: a high-performance technique of mass analysis Anal. Chem. 72 2000 1156 1162 (Pubitemid 30163769)
30. A. Makarov, E. Denisov, A. Kholomeev, W. Baischun, O. Lange, K. Strupat, and S. Horning Performance evaluation of a hybrid linear ion trap/orbitrap mass spectrometer Anal. Chem. 78 2006 2113 2120
31. TM - Hardware Manual, (2008) Revision B-1225830.
32. B.A. Patel, J.E. Dickerson, and R.F. Heck Palladium-catalyzed arylation of conjugated dienes J. Org. Chem. 43 1978 5018 5020
33. n and reaction mechanism studies by detection of transient radical cations Eur. J. Org. Chem. 2007 5162 5174