Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4726-4731

  Ishiyama, Tatsuo ^a   Kizaki, Hiroe ^a   Hayashi, Takahiro ^a   Suzuki, Akira ^a,b   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000885426     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980417b     Document Type: Article

References (69)

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34. The carbonylation of Ar-M-X complexes (M = Pd, Pt): (a) Dixon, K. R.; Dixon, A. C. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 208. (b) Anderson, G. K. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 460. (c) Alexander, J. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Vol. 2, p 349. (d) Cross, R. J.; Gemmill, J. J. Chem. Soc., Dalton Trans. 1981, 2317. (e) Sugita, N.; Minkiewicz, J. V.; Heck, R. F. Inorg. Chem. 1978, 17, 2809. (f) Garrou, P. E.; Heck, R. F. J. Am. Chem. Soc. 1976, 98, 4115.
35. The carbonylation of Ar-M-X complexes (M = Pd, Pt): (a) Dixon, K. R.; Dixon, A. C. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 208. (b) Anderson, G. K. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 460. (c) Alexander, J. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Vol. 2, p 349. (d) Cross, R. J.; Gemmill, J. J. Chem. Soc., Dalton Trans. 1981, 2317. (e) Sugita, N.; Minkiewicz, J. V.; Heck, R. F. Inorg. Chem. 1978, 17, 2809. (f) Garrou, P. E.; Heck, R. F. J. Am. Chem. Soc. 1976, 98, 4115.
36. The carbonylation of Ar-M-X complexes (M = Pd, Pt): (a) Dixon, K. R.; Dixon, A. C. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 208. (b) Anderson, G. K. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 460. (c) Alexander, J. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Vol. 2, p 349. (d) Cross, R. J.; Gemmill, J. J. Chem. Soc., Dalton Trans. 1981, 2317. (e) Sugita, N.; Minkiewicz, J. V.; Heck, R. F. Inorg. Chem. 1978, 17, 2809. (f) Garrou, P. E.; Heck, R. F. J. Am. Chem. Soc. 1976, 98, 4115.
37. The carbonylation of Ar-M-X complexes (M = Pd, Pt): (a) Dixon, K. R.; Dixon, A. C. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 208. (b) Anderson, G. K. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 460. (c) Alexander, J. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Vol. 2, p 349. (d) Cross, R. J.; Gemmill, J. J. Chem. Soc., Dalton Trans. 1981, 2317. (e) Sugita, N.; Minkiewicz, J. V.; Heck, R. F. Inorg. Chem. 1978, 17, 2809. (f) Garrou, P. E.; Heck, R. F. J. Am. Chem. Soc. 1976, 98, 4115.
38. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
39. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
40. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
41. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
42. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
43. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
44. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
45. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
46. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
47. The effect of phosphine ligands on the CO insertion of R-Pd-X complexes: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684. (b) Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K. Organometallics 1996, 15, 668. (c) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977. (d) Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937. (e) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357. (f) Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598. The effect of phosphine ligands on the alkene insertion: (g) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558. (h) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481. (i) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796. (j) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
48. The effect of halogen ligand on the carbonylation of R-M-X complexes (M = Pd, Pt): (a) Cross, R. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 407. (b) Ankersmit, H. A.; Witte, P. T.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; Goubitz, K.; Vrieze, K.; Vankoten, G. Inorg. Chem. 1996, 35, 6053. (c) Stang, P. J.; Zhong, Z.; Arif, A. M. Organometallics 1992, 11, 1017. (d) Anderson, G. K.; Cross, R. J. Acc. Chem. Res. 1984, 17, 67. (e) Anderson, G. K.; Cross, R. J. J. Chem. Soc., Dalton Trans. 1980, 712.
49. The effect of halogen ligand on the carbonylation of R-M-X complexes (M = Pd, Pt): (a) Cross, R. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 407. (b) Ankersmit, H. A.; Witte, P. T.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; Goubitz, K.; Vrieze, K.; Vankoten, G. Inorg. Chem. 1996, 35, 6053. (c) Stang, P. J.; Zhong, Z.; Arif, A. M. Organometallics 1992, 11, 1017. (d) Anderson, G. K.; Cross, R. J. Acc. Chem. Res. 1984, 17, 67. (e) Anderson, G. K.; Cross, R. J. J. Chem. Soc., Dalton Trans. 1980, 712.
50. The effect of halogen ligand on the carbonylation of R-M-X complexes (M = Pd, Pt): (a) Cross, R. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 407. (b) Ankersmit, H. A.; Witte, P. T.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; Goubitz, K.; Vrieze, K.; Vankoten, G. Inorg. Chem. 1996, 35, 6053. (c) Stang, P. J.; Zhong, Z.; Arif, A. M. Organometallics 1992, 11, 1017. (d) Anderson, G. K.; Cross, R. J. Acc. Chem. Res. 1984, 17, 67. (e) Anderson, G. K.; Cross, R. J. J. Chem. Soc., Dalton Trans. 1980, 712.
51. The effect of halogen ligand on the carbonylation of R-M-X complexes (M = Pd, Pt): (a) Cross, R. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 407. (b) Ankersmit, H. A.; Witte, P. T.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; Goubitz, K.; Vrieze, K.; Vankoten, G. Inorg. Chem. 1996, 35, 6053. (c) Stang, P. J.; Zhong, Z.; Arif, A. M. Organometallics 1992, 11, 1017. (d) Anderson, G. K.; Cross, R. J. Acc. Chem. Res. 1984, 17, 67. (e) Anderson, G. K.; Cross, R. J. J. Chem. Soc., Dalton Trans. 1980, 712.
52. The effect of halogen ligand on the carbonylation of R-M-X complexes (M = Pd, Pt): (a) Cross, R. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, p 407. (b) Ankersmit, H. A.; Witte, P. T.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; Goubitz, K.; Vrieze, K.; Vankoten, G. Inorg. Chem. 1996, 35, 6053. (c) Stang, P. J.; Zhong, Z.; Arif, A. M. Organometallics 1992, 11, 1017. (d) Anderson, G. K.; Cross, R. J. Acc. Chem. Res. 1984, 17, 67. (e) Anderson, G. K.; Cross, R. J. J. Chem. Soc., Dalton Trans. 1980, 712.
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