Transition Metal-Catalyzed Reactions of Methylenecyclopropanes

Advanced Synthesis and Catalysis

Volumn 344, Issue 2, 2002, Pages 111-129

  Nakamura, Itaru ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Catalytic reaction; Hydroamination; Hydrocarbonation; Methylenecyclopropane; Transition metals (late)

Indexed keywords

EID: 0001500173     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200202)344:2<111::AID-ADSC111>3.0.CO;2-0     Document Type: Review

References (119)

1. a) A. Brandi, A. Goti, Chem. Rev. 1998, 98, 589;
2. b) Carbocyclic Three-Membered Ring Compounds, in Houben-Weyl, Vol. E17, (Ed.: A. de Meijere), Thieme, Stuttgart, 1996.
3. P. Binger, U. Schuchardt, Chem. Ber. 1981, 114, 3313.
4. R. Noyori, T. Odagi, H. Takaya, J. Am. Chem. Soc. 1970, 92, 5780.
5. P. Binger, M. J. Doyle, R. Benn, Chem. Ber. 1983, 116, 1.
6. For a review, see: P. Binger, H. M. Büch, Top. Curr. Chem. 1987, 135, 77.
7. H. Nüske, M. Notlemeyer, A. de Meijere, Angew. Chem. Int. Ed. 2001, 40, 3411.
8. B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1.
9. B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1.
10. H. Corlay, R. T. Lewis, W. B. Motherwell, M. Shipman, Tetrahedron 1995, 51, 3303.
11. S. Yamago, E. Nakamura, J. Chem. Soc. Chem. Commun. 1988, 1112.
12. M. Lautens, Y. Ren, P. H. M. Delanghe, J. Am. Chem. Soc. 1994, 116, 8821.
13. a) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49.;
14. b) P. Binger, T. Schmidt, in Honben-Weyl, Vol. E17c, (Ed.: A. de Meijere), Thieme, Stuttgart, 1997, pp. 2217;
15. c) D. M. T. Chan, in Comprehensive Organic Synthesis, Vol. 5, (Ed.: B. M. Trost), Pergamon, Oxford, 1991, pp. 217.
16. a) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Top. Curr. Chem. 2000, 207, 89;
17. b) A. de Meijere, S. I. Kozhushkov, Eur. J. Org. Chem. 2000, 3809;
18. c) A. de Meijere, H. Nüske, M. Es-Sayed, T. Labahn, M. Schroen, S. Bräse, Angew. Chem. 1999, 111, 3881; Angew, Chem. Int. Ed. 1999, 38, 3669;
19. c) A. de Meijere, H. Nüske, M. Es-Sayed, T. Labahn, M. Schroen, S. Bräse, Angew. Chem. 1999, 111, 3881; Angew, Chem. Int. Ed. 1999, 38, 3669;
20. d) P. Binger, P. Wedemann, S. I. Kozhushkov, A. de Meijere, Eur. J. Org. Chem. 1998, 113.
21. Y. Inoue, T. Hibi, M. Satake, H. Hashimoto, J. Chem. Soc. Chem. Commun. 1979, 982.
22. P. Binger, H.-J. Weintz, Chem. Ber. 1984, 117, 654.
23. H.-J. Weintz, P. Binger, Tetrahedron Lett. 1985, 26, 4075.
24. I. Nakamura, B.-H. Oh, S. Saito, Y. Yamamoto, Angew. Chem. Int. Ed. 2001, 40, 1298.
25. T. Suzuki, H. Fujimoto, Inorg. Chem. 2000, 39, 1113.
26. B.-H. Oh, I. Nakamura, S. Saito, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6203.
27. G. Fournet, G. Balme, J. Goré, Tetrahedron 1988, 44, 5809.
28. G. Fournet, G. Balme, J. J. Barieux, J. Goré, Tetrahedron 1988, 44, 5821.
29. a) S. Bräse, A. de Meijere, Angew. Chem. Int. Ed. Engl. 1995, 34, 2545;
30. b) H. Nüske, S. Bräse, S. Kozhushkov, A. de Meijere, Chem. Eur. J., submitted.
31. A. de Meijere, S. Bräse, J. Organomet. Chem. 1999, 576, 88.
32. M. Lautens, C. Meyer, A. Lorenz, J. Am. Chem. Soc. 1996, 118, 10676.
33. A. G. Bessmertnykh, K. A. Blinov, Yu. K. Grishin, N. A. Donskaya, E. V. Tveritinova, N. M. Yur'eva, I. P. Beletskaya, J. Org. Chem. 1997, 62, 6069.
34. A. G. Bessmertnykh, K. A. Blinov, Yu. K. Grishin, N. A. Donskaya, I. P. Beletskaya, Tetrahedron Lett. 1995, 36, 7901.
35. For a review, see: Y. Yamamoto, U. Radhakrishnan, Chem. Soc. Rev. 1999, 28, 199.
36. a) K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 1183;
37. b) O. S. Andell, J.-E. Bäckvall, C. Moberg, Acta. Chem. Scand. Ser. B 1986, 40, 184;
38. c) R. Baker, R. J. Popplestone, Tetrahedron Lett. 1978, 38, 3575;
39. d)P. W. Jolly, N. Kokel, Synthesis 1990, 771;
40. e) B. M. Trost, L. Zhi, Tetrahedron Lett. 1992, 33, 1831.
41. a) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, J. Chem. Soc. Chem. Commun. 1996, 17;
42. b) V. Gevorgyan, C, Kadowaki, M. M. Salter, I. Kadota, S. Saito, Y. Yamamoto, Tetrahedron, 1997, 53, 9097.
43. a) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019;
44. b) L. Besson, J. Goré, B. Cazes, Tetrahedron Lett. 1995, 36, 3853;
45. c) B. M. Trost, V. J. Gerusz, J. Am. Chem. Soc. 1995, 117, 5156;
46. d) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811;
47. e) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969;
48. f) Y. Yamamoto, M. AlMasum, N. Fujiwara, J. Chem. Soc. Chem. Commun. 1996, 381;
49. g) Y. Yamamoto, M. Al-Masum, A. Takeda, J. Chem. Soc. Chem. Commun. 1996, 831.
50. For propargyl compounds, see: a) I. Kadota, A. Shibuya, Y.-S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262; for intramolecular hydrocarbonation of alkynes, see: b) N. Tsukada, Y. Yamamoto, Angew. Chem. Int. Ed. Engl. 1997, 36, 2477.
51. For propargyl compounds, see: a) I. Kadota, A. Shibuya, Y.-S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262; for intramolecular hydrocarbonation of alkynes, see: b) N. Tsukada, Y. Yamamoto, Angew. Chem. Int. Ed. Engl. 1997, 36, 2477.
52. a) B. M. Trost, C. Chan, G. Rühter, J. Am. Chem. Soc. 1987, 109, 3486;
53. b) B. M. Trost, S. Matsubara, J. J. Caringi, J. J. J. Am. Chem. Soc. 1989, 111, 8745; for allenes, see:
54. c) B. M. Trost, G. Kottirsch, J. Am. Chem. Soc. 1990, 112, 2816;
55. d) M. Yamaguchi, K. Omata, M. Hirama, Tetrahedron Lett. 1994, 55, 5689;
56. e) M. Yamaguchi, Y. Kido, K. Omata, M. Hirama, Synlett 1995, 1181.
57. For intramolecular reaction of aldehydes, see: a) R. C. Larock, K. Oertle, G. F. Potter, J. Am. Chem. Soc. 1980, 102, 190; b) R. E. Campbell, C. F. Lochow, K. P. Vora, R. G. Miller, J. Am. Chem. Soc. 1980, 102, 5824; for intermolecular reactions, see: c) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286; d) T. Tsuda, T. Kiyoi, T. Saegusa, J. Org. Chem. 1990, 55, 2554; e) C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1997, 119, 3165; f) C.-H. Jun, D.-Y. Lee, J.-B. Hong, Tetrahedron Lett. 1997, 38, 6673; for asymmetric addition, see: g) X. M. Wu, K. Funakoshi, K. Sakai, Tetrahedron Lett. 1993, 34, 5927; h) R. W. Barnhart, D. A. McMorran, B. Bosnich, Chem. Commun. 1997, 589.
58. For intramolecular reaction of aldehydes, see: a) R. C. Larock, K. Oertle, G. F. Potter, J. Am. Chem. Soc. 1980, 102, 190; b) R. E. Campbell, C. F. Lochow, K. P. Vora, R. G. Miller, J. Am. Chem. Soc. 1980, 102, 5824; for intermolecular reactions, see: c) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286; d) T. Tsuda, T. Kiyoi, T. Saegusa, J. Org. Chem. 1990, 55, 2554; e) C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1997, 119, 3165; f) C.-H. Jun, D.-Y. Lee, J.-B. Hong, Tetrahedron Lett. 1997, 38, 6673; for asymmetric addition, see: g) X. M. Wu, K. Funakoshi, K. Sakai, Tetrahedron Lett. 1993, 34, 5927; h) R. W. Barnhart, D. A. McMorran, B. Bosnich, Chem. Commun. 1997, 589.
59. For intramolecular reaction of aldehydes, see: a) R. C. Larock, K. Oertle, G. F. Potter, J. Am. Chem. Soc. 1980, 102, 190; b) R. E. Campbell, C. F. Lochow, K. P. Vora, R. G. Miller, J. Am. Chem. Soc. 1980, 102, 5824; for intermolecular reactions, see: c) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286; d) T. Tsuda, T. Kiyoi, T. Saegusa, J. Org. Chem. 1990, 55, 2554; e) C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1997, 119, 3165; f) C.-H. Jun, D.-Y. Lee, J.-B. Hong, Tetrahedron Lett. 1997, 38, 6673; for asymmetric addition, see: g) X. M. Wu, K. Funakoshi, K. Sakai, Tetrahedron Lett. 1993, 34, 5927; h) R. W. Barnhart, D. A. McMorran, B. Bosnich, Chem. Commun. 1997, 589.
60. For intramolecular reaction of aldehydes, see: a) R. C. Larock, K. Oertle, G. F. Potter, J. Am. Chem. Soc. 1980, 102, 190; b) R. E. Campbell, C. F. Lochow, K. P. Vora, R. G. Miller, J. Am. Chem. Soc. 1980, 102, 5824; for intermolecular reactions, see: c) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286; d) T. Tsuda, T. Kiyoi, T. Saegusa, J. Org. Chem. 1990, 55, 2554; e) C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1997, 119, 3165; f) C.-H. Jun, D.-Y. Lee, J.-B. Hong, Tetrahedron Lett. 1997, 38, 6673; for asymmetric addition, see: g) X. M. Wu, K. Funakoshi, K. Sakai, Tetrahedron Lett. 1993, 34, 5927; h) R. W. Barnhart, D. A. McMorran, B. Bosnich, Chem. Commun. 1997, 589.
61. For intramolecular reaction of aldehydes, see: a) R. C. Larock, K. Oertle, G. F. Potter, J. Am. Chem. Soc. 1980, 102, 190; b) R. E. Campbell, C. F. Lochow, K. P. Vora, R. G. Miller, J. Am. Chem. Soc. 1980, 102, 5824; for intermolecular reactions, see: c) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286; d) T. Tsuda, T. Kiyoi, T. Saegusa, J. Org. Chem. 1990, 55, 2554; e) C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1997, 119, 3165; f) C.-H. Jun, D.-Y. Lee, J.-B. Hong, Tetrahedron Lett. 1997, 38, 6673; for asymmetric addition, see: g) X. M. Wu, K. Funakoshi, K. Sakai, Tetrahedron Lett. 1993, 34, 5927; h) R. W. Barnhart, D. A. McMorran, B. Bosnich, Chem. Commun. 1997, 589.
62. For intramolecular reaction of aldehydes, see: a) R. C. Larock, K. Oertle, G. F. Potter, J. Am. Chem. Soc. 1980, 102, 190; b) R. E. Campbell, C. F. Lochow, K. P. Vora, R. G. Miller, J. Am. Chem. Soc. 1980, 102, 5824; for intermolecular reactions, see: c) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286; d) T. Tsuda, T. Kiyoi, T. Saegusa, J. Org. Chem. 1990, 55, 2554; e) C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1997, 119, 3165; f) C.-H. Jun, D.-Y. Lee, J.-B. Hong, Tetrahedron Lett. 1997, 38, 6673; for asymmetric addition, see: g) X. M. Wu, K. Funakoshi, K. Sakai, Tetrahedron Lett. 1993, 34, 5927; h) R. W. Barnhart, D. A. McMorran, B. Bosnich, Chem. Commun. 1997, 589.
63. For intramolecular reaction of aldehydes, see: a) R. C. Larock, K. Oertle, G. F. Potter, J. Am. Chem. Soc. 1980, 102, 190; b) R. E. Campbell, C. F. Lochow, K. P. Vora, R. G. Miller, J. Am. Chem. Soc. 1980, 102, 5824; for intermolecular reactions, see: c) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286; d) T. Tsuda, T. Kiyoi, T. Saegusa, J. Org. Chem. 1990, 55, 2554; e) C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1997, 119, 3165; f) C.-H. Jun, D.-Y. Lee, J.-B. Hong, Tetrahedron Lett. 1997, 38, 6673; for asymmetric addition, see: g) X. M. Wu, K. Funakoshi, K. Sakai, Tetrahedron Lett. 1993, 34, 5927; h) R. W. Barnhart, D. A. McMorran, B. Bosnich, Chem. Commun. 1997, 589.
64. For intramolecular reaction of aldehydes, see: a) R. C. Larock, K. Oertle, G. F. Potter, J. Am. Chem. Soc. 1980, 102, 190; b) R. E. Campbell, C. F. Lochow, K. P. Vora, R. G. Miller, J. Am. Chem. Soc. 1980, 102, 5824; for intermolecular reactions, see: c) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286; d) T. Tsuda, T. Kiyoi, T. Saegusa, J. Org. Chem. 1990, 55, 2554; e) C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1997, 119, 3165; f) C.-H. Jun, D.-Y. Lee, J.-B. Hong, Tetrahedron Lett. 1997, 38, 6673; for asymmetric addition, see: g) X. M. Wu, K. Funakoshi, K. Sakai, Tetrahedron Lett. 1993, 34, 5927; h) R. W. Barnhart, D. A. McMorran, B. Bosnich, Chem. Commun. 1997, 589.
65. a) S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529;
66. b) F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, S. Murai, Bull. Chem. Soc. Jpn. 1995, 68, 62.
67. G. Balavoine, C. Eskenazi, M. Guillemot, J. Chem. Soc. Chem. Commun. 1979, 1109.
68. a) P. Binger, P. Bentz, Angew. Chem. 1982, 94, 636; Angew. Chem. Int. Ed. Engl. 1982, 21, 622;
69. a) P. Binger, P. Bentz, Angew. Chem. 1982, 94, 636; Angew. Chem. Int. Ed. Engl. 1982, 21, 622;
70. [10b]
71. N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123.
72. B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1979, 101, 6432.
73. N. Tsukada, A. Shibuya, I. Nakamura, H, Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
74. a) P. Hong, B.-R. Cho, H. Yamazaki, Chem. Lett. 1980, 507.
75. 2/t-butyl perbenzoate to give the oxidative coupling products derived from formal dehydrogenation of the C-H at the 2-position and vinylic hydrogen.
76. I. Nakamura, S. Saito, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 2661.
77. R. L. Phillips, R. J. Puddephatt, J. Chem. Soc. Dalton Trans. 1978, 1736.
78. R. R. Fraser, B. Monique, T. S. Mansour, J. Chem. Soc. Chem. Commun. 1983, 620.
79. P. Binger, U. Schuchardt, Chem. Ber. 1980, 113, 3334.
80. A. D. Rodríguez, J.-G. Shi, S. D. Huang, J. Org. Chem. 1998, 63, 4425.
81. T. Bach, L. Krüger, Tetrahedron Lett. 1998, 39, 1729, and references cited therein.
82. M. Ochi, K. Yamada, H. Kawakami, A. Tatsukawa, H. Kotsuki, K. Shibata, Tetrahedron Lett. 1992, 33, 7531.
83. a) M. B. Gasc, A. Lattes, J. J. Perie, Tetrahedron 1983, 39, 703;
84. b) D. Savoia, in: Houben-Weyl, Vol. E21e, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, pp. 5356;
85. c) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675.
86. E. Haak, I. Bytschkov, S. Doye, Angew. Chem. Int. Ed. 1999, 38, 3389.
87. P. J. Walsh, A. M. Baranger, R. G. Bergman, J. Am. Chem. Soc. 1992, 114, 1708.
88. a) A. L. Casalnuovo, J. C. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738;
89. b) R. Dorta, P. Egli, F. Zürcher, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857.
90. J.-J. Brunet, G. Commenges, D. Neibecker, K. Philippot, J. Organomet. Chem. 1994, 469, 221.
91. Y. Li, T. J. Marks, Organometallics 1996, 15, 3770.
92. A. Haskel, T. Straub, M. S. Eisen, Organometallics 1996, 15, 3773.
93. R. W. Armbruster, M. M. Morgan, J. L. Schmidt, C. M. Lau, R. M. Riley, D. L. Zabrowski, H. A. Dieck, Organometallics 1986, 5, 234.
94. a) L. Besson, J. Goré, B. Cazes, Tetrahedron Lett. 1995, 36, 3857;
95. b) M. Al-Masum, M. Meguro, Y. Yamamoto, Tetrahedron Lett. 1997, 38, 6071;
96. c) M. Meguro, Y. Yamamoto, Tetrahedron Lett. 1998, 39, 5421.
97. U. Radhakrishnan, M. Al-Masum, Y. Yamamoto, Tetrahedron Lett. 1998, 39; 1037.
98. I. Kadota, A. Shibuya, L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570.
99. M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 9546.
100. I. Nakamura, H. Itagaki, Y. Yamamoto J. Org. Chem. 1998, 63, 6458.
101. a) T. Yamamoto, K. Sano, A. Yamamoto, Chem. Lett. 1982, 907;
102. b) A. L. Seligson, R. L. Cowan, W. C. Trogler, Inorg. Chem. 1991, 30, 3371.
103. a) M. S. Silver, P. R. Shafer, J. E. Nordlander, C. Rüchardt, J. D. Roberts, J. Am. Chem. Soc. 1960, 82, 2646;
104. b) P. A. Wender, H. Takahashi, B. Witulski, J. Am. Chem. Soc. 1995, 117, 4720;
105. c) G. Dyker, Angew. Chem. Int. Ed. Engl. 1995, 34, 2223.
106. a) E. J. Smutny, J. Am. Chem. Soc. 1967, 89, 6793;
107. b) H. Yagi, E. Tanaka, H. Ishiwatari, M. Hidai, Y. Uchida, Synthesis 1977, 334.
108. a) Y. Inoue, Y. Ohtsuka, H. Hashimoto, Bull. Chem. Soc. Jpn. 1984, 57, 3345;
109. b) D. R. Coulson, J. Org. Chem. 1973, 38, 1483.
110. D. H. Camacho, I. Nakamura, S. Saito, Y. Yamamoto, Angew. Chem. Int. Ed. 1999, 38, 3365.
111. 2Pd(H)(OPh)]·PhOH complex which was isolated and characterized unambiguously: a) D. Braga, P. Sabatino, C. Di Bugno, P. Leoni, M. Pasquali, J. Organomet. Chem. 1987,334, C46; b) C. Di Bugno, M. Pasquali, P. Leoni, P. Sabatino, D. Braga, Inorg. Chem. 1989, 28, 1390; for a review, see: c) V. V. Grushin, Chem. Rev. 1996, 96, 2011.
112. 2Pd(H)(OPh)]·PhOH complex which was isolated and characterized unambiguously: a) D. Braga, P. Sabatino, C. Di Bugno, P. Leoni, M. Pasquali, J. Organomet. Chem. 1987,334, C46; b) C. Di Bugno, M. Pasquali, P. Leoni, P. Sabatino, D. Braga, Inorg. Chem. 1989, 28, 1390; for a review, see: c) V. V. Grushin, Chem. Rev. 1996, 96, 2011.
113. 2Pd(H)(OPh)]·PhOH complex which was isolated and characterized unambiguously: a) D. Braga, P. Sabatino, C. Di Bugno, P. Leoni, M. Pasquali, J. Organomet. Chem. 1987,334, C46; b) C. Di Bugno, M. Pasquali, P. Leoni, P. Sabatino, D. Braga, Inorg. Chem. 1989, 28, 1390; for a review, see: c) V. V. Grushin, Chem. Rev. 1996, 96, 2011.
114. D. H. Camacho, I. Nakamura, S. Saito, Y. Yamamoto, J. Org. Chem. 2001, 66, 270.
115. For a review, see: M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221.
116. Quite recently, bicyclopropylidene 28 has also been used for catalytic bismetallation: T. Pohlmann, A. de Meijere, Org. Lett. 2000, 2, 3877.
117. N. Chatani, T. Takeyasu, T. Hanafusa, Tetrahedron Lett. 1988, 29, 3979.
118. T. Ishiyama, S. Momota, N. Miyaura, Synlett 1999, 1790.
119. M. Suginome, T. Matsuda, Y. Ito, J. Am. Chem. Soc. 2000, 122, 11015.