ESI-Mass spectrometry as a tool for investigating the mechanistic role of a 15-membered triolefinic macrocyclic palladium(0) complex in the Heck reaction

Arkivoc

Volumn 2005, Issue 9, 2005, Pages 51-62

  Pla Quintana, Anna ^a   Roglans, Anna ^a  

^a UNIVERSITY OF GIRONA   (Spain)

Author keywords

Catalysis; ESI mass spectrometry; Heck reaction; Olefinic macrocyclic complexes; Palladium; Reaction mechanisms

Indexed keywords

ALKENE DERIVATIVE; DIAZONIUM COMPOUND; MACROCYCLIC COMPOUND; ORGANOMETALLIC COMPOUND; PALLADIUM COMPLEX;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; ELECTROSPRAY MASS SPECTROMETRY; HECK REACTION; MECHANICS; REACTION ANALYSIS;

EID: 15444370241     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (37)

1. (a) Moreno-Mañas, M.; Pleixats, R.; Roglans, A.; Sebastián, R.M.; Vallribera, A. Arkivoc 2004 (iv), 109, (http://www.arkat-usa.org).
2. (b) Moreno-Mañas, M.; Pleixats, R.; Sebastián, R.M.; Vallribera, A.; Roglans, A. J. Organomet. Chem. 2004, 689, 3669.
3. Masllorens, J.; Moreno-Mañas, M.; Pla-Quintana, A.; Roglans, A. Org. Lett. 2003, 5, 1559.
4. For a monograph on ESI-MS see: Cole, R.B. Electrospray Ionization Mass Spectrometry. Fundamentals, Instrumentation and Applications, Wiley: New York, 1997.
5. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
6. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
7. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
8. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
9. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
10. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
11. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
12. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
13. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
14. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
15. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
16. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
17. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
18. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
19. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
20. For uses of ESI-MS in direct observation of reaction intermediates see: (a) Wilson, S.R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994. (b) Aliprantis, A.O.; Canary, J.W. J. Am. Chem. Soc. 1994, 116, 6985. (c) Arakawa, R.; Tachiyashiki, S.; Matsuo, T. Anal. Chem. 1995, 67, 4133. (d) Sam, J.W.; Tang, X.J.; Magliozzo, R.S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012. (e) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147. (f) Brown, J.M.; Hii, K.K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657. (g) Arakawa, R.; Matsuda, F.; Matsubayashi, G.E.; Matsuo, T. J. Am. Soc. Mass Spectrom. 1997, 8, 713. (h) Hii, K.K.; Claridge, T.D.W.; Brown, J.M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (i) Feichtinger, D.; Plattner, D.A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125. (j) Aramendía, M.A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592. (k) Volland, M.A.O.; Adlhart, C.; Kiener, C.A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621. (l) Feichtinger, D.; Plattner, D.A. Chem. Eur. J. 2001, 7, 591. (m) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J.O. Angew. Chem., Int. Ed. 2002, 41, 2738. (n) Meyer, S.; Koch, R.; Metzger, J.O. Angew. Chem. Int. Ed. 2003, 42, 4700. (o) Chen, P. Angew. Chem., Int. Ed. Engl. 2003, 42, 2832. (p) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
21. For the application of ESI-MS to inorganic and organometallic chemistry, see the following reviews and references cited therein: (a) Colton, R.; D'Agostino, A.; Traeger, J.C. Mass Spectrom. Rev. 1995, 14, 79. (b) Henderson, W.; Nicholson, B.K.; McCaffrey, L.J. Polyhedron 1998, 17, 4291. (c) Traeger, J.C. Int. J. Mass Spectrom. 2000, 200, 387. (d) Plattner, D.A. Int. J. Mass Spectrom. 2001, 207, 125. (e) Plattner, D.A. Top. Curr. Chem. 2003, 225, 153.
22. For the application of ESI-MS to inorganic and organometallic chemistry, see the following reviews and references cited therein: (a) Colton, R.; D'Agostino, A.; Traeger, J.C. Mass Spectrom. Rev. 1995, 14, 79. (b) Henderson, W.; Nicholson, B.K.; McCaffrey, L.J. Polyhedron 1998, 17, 4291. (c) Traeger, J.C. Int. J. Mass Spectrom. 2000, 200, 387. (d) Plattner, D.A. Int. J. Mass Spectrom. 2001, 207, 125. (e) Plattner, D.A. Top. Curr. Chem. 2003, 225, 153.
23. For the application of ESI-MS to inorganic and organometallic chemistry, see the following reviews and references cited therein: (a) Colton, R.; D'Agostino, A.; Traeger, J.C. Mass Spectrom. Rev. 1995, 14, 79. (b) Henderson, W.; Nicholson, B.K.; McCaffrey, L.J. Polyhedron 1998, 17, 4291. (c) Traeger, J.C. Int. J. Mass Spectrom. 2000, 200, 387. (d) Plattner, D.A. Int. J. Mass Spectrom. 2001, 207, 125. (e) Plattner, D.A. Top. Curr. Chem. 2003, 225, 153.
24. For the application of ESI-MS to inorganic and organometallic chemistry, see the following reviews and references cited therein: (a) Colton, R.; D'Agostino, A.; Traeger, J.C. Mass Spectrom. Rev. 1995, 14, 79. (b) Henderson, W.; Nicholson, B.K.; McCaffrey, L.J. Polyhedron 1998, 17, 4291. (c) Traeger, J.C. Int. J. Mass Spectrom. 2000, 200, 387. (d) Plattner, D.A. Int. J. Mass Spectrom. 2001, 207, 125. (e) Plattner, D.A. Top. Curr. Chem. 2003, 225, 153.
25. For the application of ESI-MS to inorganic and organometallic chemistry, see the following reviews and references cited therein: (a) Colton, R.; D'Agostino, A.; Traeger, J.C. Mass Spectrom. Rev. 1995, 14, 79. (b) Henderson, W.; Nicholson, B.K.; McCaffrey, L.J. Polyhedron 1998, 17, 4291. (c) Traeger, J.C. Int. J. Mass Spectrom. 2000, 200, 387. (d) Plattner, D.A. Int. J. Mass Spectrom. 2001, 207, 125. (e) Plattner, D.A. Top. Curr. Chem. 2003, 225, 153.
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34. Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.
35. 4 to the reaction mixture in order to generate cationic species by displacement of iodine atom was also unsuccessful.
36. 3].dba, in which species involving the insertion of the olefin have been detected, has been published recently (see ref. 7) .
37. Roe, A. Org. React. 1949, 44, 1572.