The palladium-iminophosphine catalyst for the reactions of organostannanes

Journal of Organometallic Chemistry

Volumn 576, Issue 1-2, 1999, Pages 169-178

  Shirakawa, Eiji ^a   Hiyama, Tamejiro ^b  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Carbostannylation; Catalytic cycle; Cross coupling; Homocoupling; Oxidative addition

Indexed keywords

EID: 0008748616     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)01056-0     Document Type: Review

References (59)

1. M. Kosugi, K. Sasazawa, Y. Shimizu, T. Migita, Chem. Lett. (1977) 301.
2. For reviews, see: (a) J.K. Stille, Angew. Chem. Int. Ed. Engl. 25 (1986) 508. (b) T.N. Mitchell, Synthesis (1992) 803. V. Farina, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon Press, New York, 1995, p. 200.
3. For reviews, see: (a) J.K. Stille, Angew. Chem. Int. Ed. Engl. 25 (1986) 508. (b) T.N. Mitchell, Synthesis (1992) 803. V. Farina, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon Press, New York, 1995, p. 200.
4. For reviews, see: (a) J.K. Stille, Angew. Chem. Int. Ed. Engl. 25 (1986) 508. (b) T.N. Mitchell, Synthesis (1992) 803. V. Farina, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon Press, New York, 1995, p. 200.
5. V. Farina, Pure Appl. Chem. 68 (1996) 73.
6. Parts of this study are already reported, (a) E. Shirakawa, H. Yoshida, H. Takaya, Tetrahedron Lett. 38 (1997) 3759. (b) E. Shirakawa, H. Yoshida, T. Hiyama, Tetrahedron Lett. 38 (1997) 5177. (c) E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 120 (1998) 2975. (d) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, Synlett (1997) 1143. (e) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, to be submitted.
7. Parts of this study are already reported, (a) E. Shirakawa, H. Yoshida, H. Takaya, Tetrahedron Lett. 38 (1997) 3759. (b) E. Shirakawa, H. Yoshida, T. Hiyama, Tetrahedron Lett. 38 (1997) 5177. (c) E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 120 (1998) 2975. (d) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, Synlett (1997) 1143. (e) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, to be submitted.
8. Parts of this study are already reported, (a) E. Shirakawa, H. Yoshida, H. Takaya, Tetrahedron Lett. 38 (1997) 3759. (b) E. Shirakawa, H. Yoshida, T. Hiyama, Tetrahedron Lett. 38 (1997) 5177. (c) E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 120 (1998) 2975. (d) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, Synlett (1997) 1143. (e) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, to be submitted.
9. Parts of this study are already reported, (a) E. Shirakawa, H. Yoshida, H. Takaya, Tetrahedron Lett. 38 (1997) 3759. (b) E. Shirakawa, H. Yoshida, T. Hiyama, Tetrahedron Lett. 38 (1997) 5177. (c) E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 120 (1998) 2975. (d) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, Synlett (1997) 1143. (e) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, to be submitted.
10. Parts of this study are already reported, (a) E. Shirakawa, H. Yoshida, H. Takaya, Tetrahedron Lett. 38 (1997) 3759. (b) E. Shirakawa, H. Yoshida, T. Hiyama, Tetrahedron Lett. 38 (1997) 5177. (c) E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 120 (1998) 2975. (d) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, Synlett (1997) 1143. (e) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, to be submitted.
11. V. Farina, B. Krishnan, J. Am. Chem. Soc. 113 (1991) 9585.
12. P. Wehman, H.M.A. van Donge, A. Hagos, P.C.J. Kamer, P.W.N.M. van Leeuwen, J. Organomet. Chem. 535 (1997) 183.
13. 2/IP.
14. The chelate coordination of a P-N ligand to Pd(II) is confirmed by X-ray diffraction studies, (a) For the Pd(II) complexes coordinated by N-(2-diphenylphosphinobenzylidene)-(S)-1-phenylethylamine, see: H.A. Ankersmit, B.H. Løken, H. Kooijman, A.L. Spek, K. Vrieze, G. van Koten, Inorg. Chim. Acta 252 (1996) 141. (b) For the Pd-AP complexes, see: W. de Graaf, S. Harder, J. Boersma, G. van Koten, J.A. Kanters, J. Organomet. Chem. 358 (1988) 545.
15. The chelate coordination of a P-N ligand to Pd(II) is confirmed by X-ray diffraction studies, (a) For the Pd(II) complexes coordinated by N-(2-diphenylphosphinobenzylidene)-(S)-1-phenylethylamine, see: H.A. Ankersmit, B.H. Løken, H. Kooijman, A.L. Spek, K. Vrieze, G. van Koten, Inorg. Chim. Acta 252 (1996) 141. (b) For the Pd-AP complexes, see: W. de Graaf, S. Harder, J. Boersma, G. van Koten, J.A. Kanters, J. Organomet. Chem. 358 (1988) 545.
16. For the coupling of organostannanes with aryl halides, bidentate ligands have been scarcely used as compared with monodentate ligands. Examples of an N-N ligand are: (a) M.E. Wright, C.K. Lowe-Ma, Organometallics 9 (1990) 347. (b) N. Tamayo, A.M. Echavarren, M.C. Paredes, F. Farina, P. Noheda, Tetrahedron Lett. 31 (1990) 5189. For the examples of P-P ligands, see: (c) D. Milstein, J.K. Stille, J. Am. Chem. Soc. 101 (1979) 4992. (d) W.J. Scott, J.K. Stille, J. Am. Chem. Soc. 108 (1986) 3033. See also Ref. [5].
17. For the coupling of organostannanes with aryl halides, bidentate ligands have been scarcely used as compared with monodentate ligands. Examples of an N-N ligand are: (a) M.E. Wright, C.K. Lowe-Ma, Organometallics 9 (1990) 347. (b) N. Tamayo, A.M. Echavarren, M.C. Paredes, F. Farina, P. Noheda, Tetrahedron Lett. 31 (1990) 5189. For the examples of P-P ligands, see: (c) D. Milstein, J.K. Stille, J. Am. Chem. Soc. 101 (1979) 4992. (d) W.J. Scott, J.K. Stille, J. Am. Chem. Soc. 108 (1986) 3033. See also Ref. [5].
18. For the coupling of organostannanes with aryl halides, bidentate ligands have been scarcely used as compared with monodentate ligands. Examples of an N-N ligand are: (a) M.E. Wright, C.K. Lowe-Ma, Organometallics 9 (1990) 347. (b) N. Tamayo, A.M. Echavarren, M.C. Paredes, F. Farina, P. Noheda, Tetrahedron Lett. 31 (1990) 5189. For the examples of P-P ligands, see: (c) D. Milstein, J.K. Stille, J. Am. Chem. Soc. 101 (1979) 4992. (d) W.J. Scott, J.K. Stille, J. Am. Chem. Soc. 108 (1986) 3033. See also Ref. [5].
19. For the coupling of organostannanes with aryl halides, bidentate ligands have been scarcely used as compared with monodentate ligands. Examples of an N-N ligand are: (a) M.E. Wright, C.K. Lowe-Ma, Organometallics 9 (1990) 347. (b) N. Tamayo, A.M. Echavarren, M.C. Paredes, F. Farina, P. Noheda, Tetrahedron Lett. 31 (1990) 5189. For the examples of P-P ligands, see: (c) D. Milstein, J.K. Stille, J. Am. Chem. Soc. 101 (1979) 4992. (d) W.J. Scott, J.K. Stille, J. Am. Chem. Soc. 108 (1986) 3033. See also Ref. [5].
20. This type of catalytic cycle was referred without any evidence by Stille and his co-workers in the palladium-catalyzed coupling of acyl chlorides with organostannanes. J.W. Labadie, J.K. Stille, J. Am. Chem. Soc. 105 (1983) 6129.
21. There have been many reports on the oxidative addition of organostannanes to a Pt(0) complex, which often shows the reactivities similar to Pd(0) complexes, (a) C. Eaborn, K. Kundu, A. Pidcock, J. Chem. Soc. Dalton Trans. (1981) 1223. (b) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 181 (1979) 47. (c) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 144 (1978) C23. (d) C. Eaborn, A. Pidcock, B.R. Steele, J. Chem. Soc. Dalton Trans. (1976) 767. (e) B. Cetinkaya, M.F. Lappert, J. McMeeking, D.E. Palmer, J. Chem. Soc. Dalton Trans. (1973) 1202.
22. There have been many reports on the oxidative addition of organostannanes to a Pt(0) complex, which often shows the reactivities similar to Pd(0) complexes, (a) C. Eaborn, K. Kundu, A. Pidcock, J. Chem. Soc. Dalton Trans. (1981) 1223. (b) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 181 (1979) 47. (c) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 144 (1978) C23. (d) C. Eaborn, A. Pidcock, B.R. Steele, J. Chem. Soc. Dalton Trans. (1976) 767. (e) B. Cetinkaya, M.F. Lappert, J. McMeeking, D.E. Palmer, J. Chem. Soc. Dalton Trans. (1973) 1202.
23. There have been many reports on the oxidative addition of organostannanes to a Pt(0) complex, which often shows the reactivities similar to Pd(0) complexes, (a) C. Eaborn, K. Kundu, A. Pidcock, J. Chem. Soc. Dalton Trans. (1981) 1223. (b) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 181 (1979) 47. (c) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 144 (1978) C23. (d) C. Eaborn, A. Pidcock, B.R. Steele, J. Chem. Soc. Dalton Trans. (1976) 767. (e) B. Cetinkaya, M.F. Lappert, J. McMeeking, D.E. Palmer, J. Chem. Soc. Dalton Trans. (1973) 1202.
24. There have been many reports on the oxidative addition of organostannanes to a Pt(0) complex, which often shows the reactivities similar to Pd(0) complexes, (a) C. Eaborn, K. Kundu, A. Pidcock, J. Chem. Soc. Dalton Trans. (1981) 1223. (b) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 181 (1979) 47. (c) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 144 (1978) C23. (d) C. Eaborn, A. Pidcock, B.R. Steele, J. Chem. Soc. Dalton Trans. (1976) 767. (e) B. Cetinkaya, M.F. Lappert, J. McMeeking, D.E. Palmer, J. Chem. Soc. Dalton Trans. (1973) 1202.
25. There have been many reports on the oxidative addition of organostannanes to a Pt(0) complex, which often shows the reactivities similar to Pd(0) complexes, (a) C. Eaborn, K. Kundu, A. Pidcock, J. Chem. Soc. Dalton Trans. (1981) 1223. (b) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 181 (1979) 47. (c) G. Butler, C. Eaborn, A. Pidcock, J. Organomet. Chem. 144 (1978) C23. (d) C. Eaborn, A. Pidcock, B.R. Steele, J. Chem. Soc. Dalton Trans. (1976) 767. (e) B. Cetinkaya, M.F. Lappert, J. McMeeking, D.E. Palmer, J. Chem. Soc. Dalton Trans. (1973) 1202.
26. 1H}-NMR (THF): δ 23.2 for 4; δ - 9.2 (J = 53 Hz), 10.1 (J = 53 Hz) for 5.
27. All attempts to isolate these complexes failed because of their instability.
28. The procedures for the generation of the Pd(0) complexes depicted in Figs. 3 and 4 were kindly suggested by Professor Tamio Hayashi (Kyoto University).
29. P. Knochel, in: B.M. Trost, I. Fleming, M.F. Semmelhack (Eds.), Comprehensive Organic Synthesis, vol. 4, Pergamon Press, New York, 1991, p. 865.
30. J.F. Normant, A. Alexakis, Synthesis (1981) 841.
31. (a) E. Negishi, T. Takahashi, Synthesis (1988) 1. (b) D.E. van Horn, E. Negishi, Pure Appl. Chem. 53 (1981) 2333.
32. (a) E. Negishi, T. Takahashi, Synthesis (1988) 1. (b) D.E. van Horn, E. Negishi, Pure Appl. Chem. 53 (1981) 2333.
33. T. Studie;demann, P. Knochel, Angew. Chem. Int. Ed. Engl. 36 (1997) 93.
34. M. Pereyre, J.-P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987.
35. Carbostannylation of alkynes using a particular combination of substrates, (stannylethynyl)amines and dimethyl acetylenedicarboxylate, is reported. G. Himbert, J. Chem. Res. (S) (1979) 88.
36. 4 is considered to proceed through carbostannylation of stannylacetylenes. (a) A. Hayashi, M. Yamaguchi, M. Hirama, C. Kabuto, M. Ueno, Chem. Lett. (1993) 1881. (b) M. Yamaguchi, A. Hayashi, M. Hirama, J. Am. Chem. Soc. 115 (1993) 3362. (c) M. Yamaguchi, A. Hayashi, M. Hirama, J. Am. Chem. Soc. 117 (1995) 1151.
37. 4 is considered to proceed through carbostannylation of stannylacetylenes. (a) A. Hayashi, M. Yamaguchi, M. Hirama, C. Kabuto, M. Ueno, Chem. Lett. (1993) 1881. (b) M. Yamaguchi, A. Hayashi, M. Hirama, J. Am. Chem. Soc. 115 (1993) 3362. (c) M. Yamaguchi, A. Hayashi, M. Hirama, J. Am. Chem. Soc. 117 (1995) 1151.
38. 4 is considered to proceed through carbostannylation of stannylacetylenes. (a) A. Hayashi, M. Yamaguchi, M. Hirama, C. Kabuto, M. Ueno, Chem. Lett. (1993) 1881. (b) M. Yamaguchi, A. Hayashi, M. Hirama, J. Am. Chem. Soc. 115 (1993) 3362. (c) M. Yamaguchi, A. Hayashi, M. Hirama, J. Am. Chem. Soc. 117 (1995) 1151.
39. Carbostannylation may alternatively be accomplished by carbocupration of alkynes followed by quenching with tin halides/ triflate. H. Westmijze, J. Meijer, P. Vermeer, Reel. Trav. Chim. Pays-Bas 96 (1977) 194.
40. 1H-NMR. The (Ζ)-Configuration of the alkenylstannane was confirmed after the transformation to the corresponding alkenyl iodide by iodolysis (see Scheme 12). The coupling constant between the olefinic protons of the alkenyl iodide was 8.3 Hz, typical of a cis-disubstituted ethylene. Iodolysis of α- or β-(alkynyl)alkenylstannanes to the corresponding (alkynyl)alkenyl iodides proceeds with retention of configuration: B.C. Stracker, G. Zweifel, Tetrahedron Lett. 32 (1991) 3329.
41. The yield based on alkynylstannane should be less than 95%, because 5% of alkynylstannane must be consumed for the reduction of Pd(II) to Pd(0).
42. 3) was equally effective.
43. 2 moiety, whereas the same reaction of B gave trans-olefms. Syn -addition in the use of acetylene led us to the conclusion that both A and B are also syn.
44. The palladium-catalyzed hydrostannylation-cyclization of 1,6-diynes is discussed to proceed in dual pathways (hydropalladation and stannylpalladation). M. Lautens, N.D. Smith, D. Ostrovsky, J. Org. Chem. 62 (1997) 8970.
45. 2-IP complex (5 mol % of Pd, Pd/IP = 1) gave the (Ζ)-alkenylarene only in 50% yield along with the correspond-ing (Ε)-isomer (10%).
46. Stoichiometric amount of copper(II) nitrate is shown to mediate the homocoupling of organostannanes. S. Ghosal, G.P. Luke, K.S. Kyler, J. Org. Chem. 52 (1987) 4296.
47. Although the homocoupling reaction of organostannanes is recorded in some papers, the products are deemed to be the side products of the corresponding cross-coupling reaction with aryl halides. For example, see: (a) V. Farina, B. Krishnan, D.R. Marshall, G.P. Roth, J. Org. Chem. 58 (1993) 5434. (b) R. van Asselt, C.J. Elsevier, Organometallics 13 (1994) 1972.
48. Although the homocoupling reaction of organostannanes is recorded in some papers, the products are deemed to be the side products of the corresponding cross-coupling reaction with aryl halides. For example, see: (a) V. Farina, B. Krishnan, D.R. Marshall, G.P. Roth, J. Org. Chem. 58 (1993) 5434. (b) R. van Asselt, C.J. Elsevier, Organometallics 13 (1994) 1972.
49. S. Kanemoto, S. Matsubara, K. Oshima, K. Utimoto, H. Nozaki, Chem. Lett. (1987) 5.
50. L.S. Liebeskind, S.W. Riesinger, Tetrahedron Lett. 32 (1991) 5681.
51. S.-K. Kang, E.-Y. Namkoong, T. Yamaguchi, Synth. Commun. 27 (1997) 641.
52. S. Yamaguchi, S. Ohno, K. Tamao, Synlett (1997) 1199.
53. M.E. Wright, M.J. Porsch, C. Buckley, B.B. Cochran, J. Am. Chem. Soc. 119 (1997) 8393.
54. G.A. Tolstikov, M.S. Miftakhov, N.A. Danilova, Y.L. Vel'der, L.V. Spirikhin, Synthesis (1989) 633.
55. Alcaraz and his co-workers independently reported that oxygen worked as an oxidant for the palladium-catalyzed homocoupling of organostannanes. L. Alcaraz, J.K. Taylor, Synlett (1997) 791.
56. 3, respectively.
57. N,N-Dimethylformamide is an effective solvent for the copper(I)-promoted homocoupling of organosilanes. K. Ikegashira, Y. Nishihara, K. Hirabayashi, A. Mori, T. Hiyama, Chem. Commun. (1997) 1039.
58. (a) L.D. Valle, J.K. Stille, L.S. Hegedus, J. Org. Chem. 55 (1990) 3019. (b) B.M. Trost, E. Keinan, Tetrahedron Lett. 22 (1980) 2595.
59. (a) L.D. Valle, J.K. Stille, L.S. Hegedus, J. Org. Chem. 55 (1990) 3019. (b) B.M. Trost, E. Keinan, Tetrahedron Lett. 22 (1980) 2595.