A soluble fluorous palladium complex that promotes heck reactions and can be recovered and reused

Synlett

Volumn , Issue 8, 2004, Pages 1379-1382

  Curran, Dennis P ^a   Fischer, Karin ^a   Moura Letts, Gustavo ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Catalysis; Fluorous chemistry; Heck reaction; Palladium pincer complex; Solid phase extraction

Indexed keywords

FLUORINE DERIVATIVE; METAL COMPLEX; PALLADIUM COMPLEX;

ARTICLE; COMPLEX FORMATION; HEAT TREATMENT; HECK REACTION; MICROWAVE RADIATION; PRECURSOR; SOLID PHASE EXTRACTION; SYNTHESIS;

EID: 3142760135     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829094     Document Type: Article

References (51)

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8. Representative recent references: (a) Dienophiles: Werner, S.; Curran, D. P. Org. Lett. 2003, 5, 3293. (b)FCBz groups: Curran, D. P.; Amatore, M.; Guthrie, D.; Campbell, M.; Go, E.; Luo, Z. Y. J. Org. Chem. 2003, 68, 4643. (c) Tin reagents: Bucher, B.; Curran, D. P. Tetrahedron Lett. 2000, 41, 9617. (d) FDEAD: Dandapani, S.; Curran, D. P. Tetrahedron 2002, 58, 3855. (e) Ester: Chen, C. H. T.; Zhang, W. Org. Lett. 2003, 5, 1015. (f) Scavengers: Zhang, W.; Chen, C. H. T.; Nagashima, T. Tetrahedron Lett. 2003, 44, 2065. (g) Acetals: Read, R. W.; Zhang, C. T. Tetrahedron Lett. 2003, 44, 7045.
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11. Representative recent references: (a) Dienophiles: Werner, S.; Curran, D. P. Org. Lett. 2003, 5, 3293. (b)FCBz groups: Curran, D. P.; Amatore, M.; Guthrie, D.; Campbell, M.; Go, E.; Luo, Z. Y. J. Org. Chem. 2003, 68, 4643. (c) Tin reagents: Bucher, B.; Curran, D. P. Tetrahedron Lett. 2000, 41, 9617. (d) FDEAD: Dandapani, S.; Curran, D. P. Tetrahedron 2002, 58, 3855. (e) Ester: Chen, C. H. T.; Zhang, W. Org. Lett. 2003, 5, 1015. (f) Scavengers: Zhang, W.; Chen, C. H. T.; Nagashima, T. Tetrahedron Lett. 2003, 44, 2065. (g) Acetals: Read, R. W.; Zhang, C. T. Tetrahedron Lett. 2003, 44, 7045.
12. Representative recent references: (a) Dienophiles: Werner, S.; Curran, D. P. Org. Lett. 2003, 5, 3293. (b)FCBz groups: Curran, D. P.; Amatore, M.; Guthrie, D.; Campbell, M.; Go, E.; Luo, Z. Y. J. Org. Chem. 2003, 68, 4643. (c) Tin reagents: Bucher, B.; Curran, D. P. Tetrahedron Lett. 2000, 41, 9617. (d) FDEAD: Dandapani, S.; Curran, D. P. Tetrahedron 2002, 58, 3855. (e) Ester: Chen, C. H. T.; Zhang, W. Org. Lett. 2003, 5, 1015. (f) Scavengers: Zhang, W.; Chen, C. H. T.; Nagashima, T. Tetrahedron Lett. 2003, 44, 2065. (g) Acetals: Read, R. W.; Zhang, C. T. Tetrahedron Lett. 2003, 44, 7045.
13. Representative recent references: (a) Dienophiles: Werner, S.; Curran, D. P. Org. Lett. 2003, 5, 3293. (b)FCBz groups: Curran, D. P.; Amatore, M.; Guthrie, D.; Campbell, M.; Go, E.; Luo, Z. Y. J. Org. Chem. 2003, 68, 4643. (c) Tin reagents: Bucher, B.; Curran, D. P. Tetrahedron Lett. 2000, 41, 9617. (d) FDEAD: Dandapani, S.; Curran, D. P. Tetrahedron 2002, 58, 3855. (e) Ester: Chen, C. H. T.; Zhang, W. Org. Lett. 2003, 5, 1015. (f) Scavengers: Zhang, W.; Chen, C. H. T.; Nagashima, T. Tetrahedron Lett. 2003, 44, 2065. (g) Acetals: Read, R. W.; Zhang, C. T. Tetrahedron Lett. 2003, 44, 7045.
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23. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
24. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
25. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
26. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
27. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
28. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
29. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
30. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
31. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
32. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
33. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
34. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
35. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
36. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
37. For work on heavy fluorous palladium complexes, see: (a) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623. (b) Betzemeier, B.; Lhermitte, F.; Knochel, P. Tetrahedron Lett. 1998, 39, 6667. (c) Shezad, N.; Oakes, R. S.; Clifford, A. A.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 2221. (d) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439. (e) Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683. (f) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243. (g) Schneider, S.; Bannwarth, W. Angew. Chem. Int. Ed. 2000, 39, 4142. (h) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301. (i) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735. (j) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524. (k) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007. (l) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993. (m) Markert, C.; Bannwarth, W. Helv. Chim. Acta 2002, 85, 1877. (n) Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39. (o) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
38. van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
39. (a) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y. S. J. Am. Chem. Soc. 1999, 121, 9531.
40. (b) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287.
41. (a) This bromide, FluoroFlash silica gel and complex 3 are commercially available from Fluorous Technologies, Inc., www.fluorous.com.
42. (b) DPC holds an equity interest in this company.
43. 13). MS (APCl, pos. mode): m/z = 1063 (M - Cl).
44. 1/n with three crystallographically independent but chemically similar molecules per asymmetric unit. The metric symmetry is suggestive of orthorhombic, with β equal to 90.02 (2)° but the crystal packing does not show any symmetry higher than monoclinic. Each molecule consists of a Pd atom coordinated to a tridentate 1,3-bis(thiomethyl)benzene SCS ligand with a Pd-Cl bond trans to the Pd-C bond. The environment about Pd is slightly distorted square planar. Distortions are caused by the rigid SCS ligand, which results in non-linear S-Pd-S angles of 171.07 (7)°, 170.11 (7)° and 167.40 (7)° in the three independent molecules of 3. Pd-Cl bonds average 2.391 (2) Å, Pd-S bonds average 2.302 (2) Å, and Pd-C bonds average 1.977 (8) Å. All three molecules have similar, well resolved Pd(SCS)Cl cores, but differ in the orientation of the fluoroalkylaryl groups attached to S. For all molecules, the two fluoroalkylaryl groups are on opposite sides of the Pd(SCS)Cl plane. Differences lie in the twisting of the aryl rings. In two of the three molecules, one of the fluoroalkyl chains is highly disordered and some fluorines and carbons at the ends of these chains cannot be resolved.
45. (a) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717.
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47. (c) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583.
48. The recovered complex exhibited the same spectra as that starting complex and had a bromine content of <0.15% by elemental analysis.
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