A bimetallic catalyst and dual role catalyst: Synthesis of N-(alkoxycarbonyl)indoles from 2-(alkynyl)phenylisocyanates

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4764-4771

  Kamijo, Shin ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIMETALLIC CATALYSTS;

ACIDS; CATALYST ACTIVITY; CATALYSTS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

ALCOHOL DERIVATIVE; ALKYNE; CARBONIC ACID DERIVATIVE; COPPER CHLORIDE; INDOLE DERIVATIVE; ISOCYANATE; ISOCYANIC ACID DERIVATIVE; LEWIS ACID; METAL; N (CARBONYL)INDOLE DERIVATIVE; PALLADIUM; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 0037603145     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034254p     Document Type: Article

References (176)

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73. For transition-metal-catalyzed or -mediated cyclizations of isocyanides, see the following. [Cu]: (a) Ito, Y.; Inubushi, Y.; Sugaya, T.; Kobayashi, K.; Saegusa, T. Bull. Chem. Soc. Jpn. 1978, 54, 1186-1188. (b) Ito, Y.; Kobayashi, K.; Saegusa, T. J. Org. Chem. 1979, 44, 2030-2032. [Ru]: (c) Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640-5641. (d) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385-396. [Cr, Mo]: (e) Aumann, R.; Kuckert, E.; Heien, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 978-979. (f) Aumann, R.; Heinen, H. Chem. Ber. 1986, 119, 2289-2307. (g) Aumann, R.; Heinen, H.; Krüger, C.; Tsay, Y.-H. Chem. Ber. 1986, 119, 3141-3149.
74. For transition-metal-catalyzed or -mediated cyclizations of isocyanides, see the following. [Cu]: (a) Ito, Y.; Inubushi, Y.; Sugaya, T.; Kobayashi, K.; Saegusa, T. Bull. Chem. Soc. Jpn. 1978, 54, 1186-1188. (b) Ito, Y.; Kobayashi, K.; Saegusa, T. J. Org. Chem. 1979, 44, 2030-2032. [Ru]: (c) Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640-5641. (d) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385-396. [Cr, Mo]: (e) Aumann, R.; Kuckert, E.; Heien, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 978-979. (f) Aumann, R.; Heinen, H. Chem. Ber. 1986, 119, 2289-2307. (g) Aumann, R.; Heinen, H.; Krüger, C.; Tsay, Y.-H. Chem. Ber. 1986, 119, 3141-3149.
75. For transition-metal-catalyzed or -mediated cyclizations of isocyanides, see the following. [Cu]: (a) Ito, Y.; Inubushi, Y.; Sugaya, T.; Kobayashi, K.; Saegusa, T. Bull. Chem. Soc. Jpn. 1978, 54, 1186-1188. (b) Ito, Y.; Kobayashi, K.; Saegusa, T. J. Org. Chem. 1979, 44, 2030-2032. [Ru]: (c) Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640-5641. (d) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385-396. [Cr, Mo]: (e) Aumann, R.; Kuckert, E.; Heien, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 978-979. (f) Aumann, R.; Heinen, H. Chem. Ber. 1986, 119, 2289-2307. (g) Aumann, R.; Heinen, H.; Krüger, C.; Tsay, Y.-H. Chem. Ber. 1986, 119, 3141-3149.
76. For transition-metal-catalyzed or -mediated cyclizations of isocyanides, see the following. [Cu]: (a) Ito, Y.; Inubushi, Y.; Sugaya, T.; Kobayashi, K.; Saegusa, T. Bull. Chem. Soc. Jpn. 1978, 54, 1186-1188. (b) Ito, Y.; Kobayashi, K.; Saegusa, T. J. Org. Chem. 1979, 44, 2030-2032. [Ru]: (c) Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640-5641. (d) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385-396. [Cr, Mo]: (e) Aumann, R.; Kuckert, E.; Heien, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 978-979. (f) Aumann, R.; Heinen, H. Chem. Ber. 1986, 119, 2289-2307. (g) Aumann, R.; Heinen, H.; Krüger, C.; Tsay, Y.-H. Chem. Ber. 1986, 119, 3141-3149.
77. For transition-metal-catalyzed or -mediated cyclizations of isocyanides, see the following. [Cu]: (a) Ito, Y.; Inubushi, Y.; Sugaya, T.; Kobayashi, K.; Saegusa, T. Bull. Chem. Soc. Jpn. 1978, 54, 1186-1188. (b) Ito, Y.; Kobayashi, K.; Saegusa, T. J. Org. Chem. 1979, 44, 2030-2032. [Ru]: (c) Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640-5641. (d) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385-396. [Cr, Mo]: (e) Aumann, R.; Kuckert, E.; Heien, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 978-979. (f) Aumann, R.; Heinen, H. Chem. Ber. 1986, 119, 2289-2307. (g) Aumann, R.; Heinen, H.; Krüger, C.; Tsay, Y.-H. Chem. Ber. 1986, 119, 3141-3149.
78. For transition-metal-catalyzed or -mediated cyclizations of isocyanides, see the following. [Cu]: (a) Ito, Y.; Inubushi, Y.; Sugaya, T.; Kobayashi, K.; Saegusa, T. Bull. Chem. Soc. Jpn. 1978, 54, 1186-1188. (b) Ito, Y.; Kobayashi, K.; Saegusa, T. J. Org. Chem. 1979, 44, 2030-2032. [Ru]: (c) Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640-5641. (d) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385-396. [Cr, Mo]: (e) Aumann, R.; Kuckert, E.; Heien, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 978-979. (f) Aumann, R.; Heinen, H. Chem. Ber. 1986, 119, 2289-2307. (g) Aumann, R.; Heinen, H.; Krüger, C.; Tsay, Y.-H. Chem. Ber. 1986, 119, 3141-3149.
79. For anionic cyclizations of isocyanides, see: (a) Ito, Y.; Kobayashi, K.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 3532-3534. (b) Ito, Y.; Kobayashi, K.; Seko, N.; Saegusa, T. Bull. Chem. Soc. Jpn. 1984, 57, 73-84. (c) Haeflinger, W.; Knecht, H. Tetrahedron Lett. 1984, 25, 289-292.
80. For anionic cyclizations of isocyanides, see: (a) Ito, Y.; Kobayashi, K.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 3532-3534. (b) Ito, Y.; Kobayashi, K.; Seko, N.; Saegusa, T. Bull. Chem. Soc. Jpn. 1984, 57, 73-84. (c) Haeflinger, W.; Knecht, H. Tetrahedron Lett. 1984, 25, 289-292.
81. For anionic cyclizations of isocyanides, see: (a) Ito, Y.; Kobayashi, K.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 3532-3534. (b) Ito, Y.; Kobayashi, K.; Seko, N.; Saegusa, T. Bull. Chem. Soc. Jpn. 1984, 57, 73-84. (c) Haeflinger, W.; Knecht, H. Tetrahedron Lett. 1984, 25, 289-292.
82. For radical cyclizations of isocyanides, see: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127-3128. (b) Shinada, T.; Miyachi, M.; Itagaki, Y.; Naoki, H.; Yoshihara, K.; Nakajima, T. Tetrahedron Lett. 1996, 37, 7099-7102. (c) Kobayashi, Y.; Fukuyama, T. J. Heterocycl. Chem. 1998, 35, 1043-1055. (d) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325-6327. (e) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216.
83. For radical cyclizations of isocyanides, see: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127-3128. (b) Shinada, T.; Miyachi, M.; Itagaki, Y.; Naoki, H.; Yoshihara, K.; Nakajima, T. Tetrahedron Lett. 1996, 37, 7099-7102. (c) Kobayashi, Y.; Fukuyama, T. J. Heterocycl. Chem. 1998, 35, 1043-1055. (d) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325-6327. (e) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216.
84. For radical cyclizations of isocyanides, see: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127-3128. (b) Shinada, T.; Miyachi, M.; Itagaki, Y.; Naoki, H.; Yoshihara, K.; Nakajima, T. Tetrahedron Lett. 1996, 37, 7099-7102. (c) Kobayashi, Y.; Fukuyama, T. J. Heterocycl. Chem. 1998, 35, 1043-1055. (d) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325-6327. (e) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216.
85. For radical cyclizations of isocyanides, see: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127-3128. (b) Shinada, T.; Miyachi, M.; Itagaki, Y.; Naoki, H.; Yoshihara, K.; Nakajima, T. Tetrahedron Lett. 1996, 37, 7099-7102. (c) Kobayashi, Y.; Fukuyama, T. J. Heterocycl. Chem. 1998, 35, 1043-1055. (d) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325-6327. (e) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216.
86. For radical cyclizations of isocyanides, see: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127-3128. (b) Shinada, T.; Miyachi, M.; Itagaki, Y.; Naoki, H.; Yoshihara, K.; Nakajima, T. Tetrahedron Lett. 1996, 37, 7099-7102. (c) Kobayashi, Y.; Fukuyama, T. J. Heterocycl. Chem. 1998, 35, 1043-1055. (d) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325-6327. (e) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216.
87. Kamijo, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 3230-3233.
88. (a) Metal-catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
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98. Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309-3310.
99. For the formation of 3-allylindoles, see: (a) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (b) ref 13a.
100. For the formation of 3-allylindoles, see: (a) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (b) ref 13a.
101. The activations of alkyl isocyanates and carbodiimides by CuCl were reported, see: (a) Schmidt, V. E.; Moosmüller, F. Liebigs Ann. Chem. 1955, 597, 235-240. (b) Corey, E. J.; Andersen, N. H.; Carlson, R. M.; Paust, J.; Vedejs, E.; Vlattas, I.; Winter, R. E. K. J. Am. Chem. Soc. 1968, 90, 3245-3247. (c) Duggan, M. E.; Imagire, J. S. Synthesis 1989, 131-132.
102. The activations of alkyl isocyanates and carbodiimides by CuCl were reported, see: (a) Schmidt, V. E.; Moosmüller, F. Liebigs Ann. Chem. 1955, 597, 235-240. (b) Corey, E. J.; Andersen, N. H.; Carlson, R. M.; Paust, J.; Vedejs, E.; Vlattas, I.; Winter, R. E. K. J. Am. Chem. Soc. 1968, 90, 3245-3247. (c) Duggan, M. E.; Imagire, J. S. Synthesis 1989, 131-132.
103. The activations of alkyl isocyanates and carbodiimides by CuCl were reported, see: (a) Schmidt, V. E.; Moosmüller, F. Liebigs Ann. Chem. 1955, 597, 235-240. (b) Corey, E. J.; Andersen, N. H.; Carlson, R. M.; Paust, J.; Vedejs, E.; Vlattas, I.; Winter, R. E. K. J. Am. Chem. Soc. 1968, 90, 3245-3247. (c) Duggan, M. E.; Imagire, J. S. Synthesis 1989, 131-132.
104. For the palladium-catalyzed reaction of isocyanates, see: (a) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157-1158. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792-3794. (c) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933-7935. (d) Trost, B. M.; Hurnaus, R. Tetrahedron Lett. 1989, 30, 3893-3896. (e) Xu, D.; Sharpless, B. Tetrahedron Lett. 1993, 34, 951-952. (f) Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173-1177. (g) Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709-3715. (h) Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152-4158.
105. For the palladium-catalyzed reaction of isocyanates, see: (a) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157-1158. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792-3794. (c) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933-7935. (d) Trost, B. M.; Hurnaus, R. Tetrahedron Lett. 1989, 30, 3893-3896. (e) Xu, D.; Sharpless, B. Tetrahedron Lett. 1993, 34, 951-952. (f) Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173-1177. (g) Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709-3715. (h) Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152-4158.
106. For the palladium-catalyzed reaction of isocyanates, see: (a) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157-1158. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792-3794. (c) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933-7935. (d) Trost, B. M.; Hurnaus, R. Tetrahedron Lett. 1989, 30, 3893-3896. (e) Xu, D.; Sharpless, B. Tetrahedron Lett. 1993, 34, 951-952. (f) Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173-1177. (g) Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709-3715. (h) Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152-4158.
107. For the palladium-catalyzed reaction of isocyanates, see: (a) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157-1158. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792-3794. (c) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933-7935. (d) Trost, B. M.; Hurnaus, R. Tetrahedron Lett. 1989, 30, 3893-3896. (e) Xu, D.; Sharpless, B. Tetrahedron Lett. 1993, 34, 951-952. (f) Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173-1177. (g) Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709-3715. (h) Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152-4158.
108. For the palladium-catalyzed reaction of isocyanates, see: (a) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157-1158. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792-3794. (c) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933-7935. (d) Trost, B. M.; Hurnaus, R. Tetrahedron Lett. 1989, 30, 3893-3896. (e) Xu, D.; Sharpless, B. Tetrahedron Lett. 1993, 34, 951-952. (f) Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173-1177. (g) Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709-3715. (h) Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152-4158.
109. For the palladium-catalyzed reaction of isocyanates, see: (a) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157-1158. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792-3794. (c) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933-7935. (d) Trost, B. M.; Hurnaus, R. Tetrahedron Lett. 1989, 30, 3893-3896. (e) Xu, D.; Sharpless, B. Tetrahedron Lett. 1993, 34, 951-952. (f) Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173-1177. (g) Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709-3715. (h) Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152-4158.
110. For the palladium-catalyzed reaction of isocyanates, see: (a) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157-1158. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792-3794. (c) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933-7935. (d) Trost, B. M.; Hurnaus, R. Tetrahedron Lett. 1989, 30, 3893-3896. (e) Xu, D.; Sharpless, B. Tetrahedron Lett. 1993, 34, 951-952. (f) Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173-1177. (g) Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709-3715. (h) Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152-4158.
111. For the palladium-catalyzed reaction of isocyanates, see: (a) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157-1158. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792-3794. (c) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933-7935. (d) Trost, B. M.; Hurnaus, R. Tetrahedron Lett. 1989, 30, 3893-3896. (e) Xu, D.; Sharpless, B. Tetrahedron Lett. 1993, 34, 951-952. (f) Ohe, K.; Matsuda, H.; Ishihara, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Org. Chem. 1993, 58, 1173-1177. (g) Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709-3715. (h) Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152-4158.
112. For the chemistry on bis-π-allylpalladium complexes, see: (a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647. (b) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114. (c) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 729-731. (d) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413-4421. (e) Nakamura, H.; Aoyagi, K.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 372-377. (f) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454. (g) Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909-912. (h) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563-1566.
113. For the chemistry on bis-π-allylpalladium complexes, see: (a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647. (b) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114. (c) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 729-731. (d) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413-4421. (e) Nakamura, H.; Aoyagi, K.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 372-377. (f) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454. (g) Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909-912. (h) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563-1566.
114. For the chemistry on bis-π-allylpalladium complexes, see: (a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647. (b) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114. (c) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 729-731. (d) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413-4421. (e) Nakamura, H.; Aoyagi, K.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 372-377. (f) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454. (g) Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909-912. (h) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563-1566.
115. For the chemistry on bis-π-allylpalladium complexes, see: (a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647. (b) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114. (c) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 729-731. (d) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413-4421. (e) Nakamura, H.; Aoyagi, K.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 372-377. (f) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454. (g) Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909-912. (h) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563-1566.
116. For the chemistry on bis-π-allylpalladium complexes, see: (a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647. (b) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114. (c) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 729-731. (d) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413-4421. (e) Nakamura, H.; Aoyagi, K.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 372-377. (f) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454. (g) Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909-912. (h) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563-1566.
117. For the chemistry on bis-π-allylpalladium complexes, see: (a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647. (b) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114. (c) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 729-731. (d) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413-4421. (e) Nakamura, H.; Aoyagi, K.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 372-377. (f) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454. (g) Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909-912. (h) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563-1566.
118. For the chemistry on bis-π-allylpalladium complexes, see: (a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647. (b) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114. (c) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 729-731. (d) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413-4421. (e) Nakamura, H.; Aoyagi, K.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 372-377. (f) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454. (g) Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909-912. (h) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563-1566.
119. For the chemistry on bis-π-allylpalladium complexes, see: (a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647. (b) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114. (c) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 729-731. (d) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413-4421. (e) Nakamura, H.; Aoyagi, K.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 372-377. (f) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454. (g) Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909-912. (h) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563-1566.
120. Anionic cyclization of 2-alkynylaniline derivatives is well-known; see: (a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 1845-1847. (b) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 1823-1828. (c) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305-1308. (d) Kondo, Y.; Kojima, S.; Sakamoto, T. Heterocycles 1996, 43, 2741-2746. (e) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (f) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (g) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490.
121. Anionic cyclization of 2-alkynylaniline derivatives is well-known; see: (a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 1845-1847. (b) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 1823-1828. (c) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305-1308. (d) Kondo, Y.; Kojima, S.; Sakamoto, T. Heterocycles 1996, 43, 2741-2746. (e) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (f) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (g) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490.
122. Anionic cyclization of 2-alkynylaniline derivatives is well-known; see: (a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 1845-1847. (b) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 1823-1828. (c) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305-1308. (d) Kondo, Y.; Kojima, S.; Sakamoto, T. Heterocycles 1996, 43, 2741-2746. (e) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (f) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (g) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490.
123. Anionic cyclization of 2-alkynylaniline derivatives is well-known; see: (a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 1845-1847. (b) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 1823-1828. (c) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305-1308. (d) Kondo, Y.; Kojima, S.; Sakamoto, T. Heterocycles 1996, 43, 2741-2746. (e) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (f) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (g) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490.
124. Anionic cyclization of 2-alkynylaniline derivatives is well-known; see: (a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 1845-1847. (b) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 1823-1828. (c) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305-1308. (d) Kondo, Y.; Kojima, S.; Sakamoto, T. Heterocycles 1996, 43, 2741-2746. (e) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (f) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (g) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490.
125. Anionic cyclization of 2-alkynylaniline derivatives is well-known; see: (a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 1845-1847. (b) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 1823-1828. (c) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305-1308. (d) Kondo, Y.; Kojima, S.; Sakamoto, T. Heterocycles 1996, 43, 2741-2746. (e) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (f) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (g) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490.
126. Anionic cyclization of 2-alkynylaniline derivatives is well-known; see: (a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 1845-1847. (b) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 1823-1828. (c) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305-1308. (d) Kondo, Y.; Kojima, S.; Sakamoto, T. Heterocycles 1996, 43, 2741-2746. (e) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (f) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534. (g) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490.
127. 41
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136. 4 (1 mol %) and CuCl (4 mol %) in THF at 100 °C for 1 h, a similar condition as shown in Table 2, did not afford the indole 3a. A significant amount of the starting material 4a was recovered, indicating that the existence of the intermediates C-F in the catalytic cycle is important for the formation of the indole.
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149. For Lewis acid-catalyzed reactions of alkynes, see: (a) Imamura, K.-i.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4081-1084. (b) Jung, I. N.; Yoo, B. R. Synlett 1999, 519-528 and references therein. (c) Asao, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 1071-1087 and references therein. (d) Yoshikawa, E.; Kasahara, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 4499-4502.
150. For Lewis acid-catalyzed reactions of alkynes, see: (a) Imamura, K.-i.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4081-1084. (b) Jung, I. N.; Yoo, B. R. Synlett 1999, 519-528 and references therein. (c) Asao, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 1071-1087 and references therein. (d) Yoshikawa, E.; Kasahara, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 4499-4502.
151. For Lewis acid-catalyzed reactions of alkynes, see: (a) Imamura, K.-i.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4081-1084. (b) Jung, I. N.; Yoo, B. R. Synlett 1999, 519-528 and references therein. (c) Asao, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 1071-1087 and references therein. (d) Yoshikawa, E.; Kasahara, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 4499-4502.
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173. The indole synthesis from 2-alkynyl-N-(alkoxycarbonyl)aniline derivatives has been reported but a cyclization with complete retention of the alkoxycarbonyl group is rare; see: (a) Reference 13a. (b) Reference 15b.
174. The indole synthesis from 2-alkynyl-N-(alkoxycarbonyl)aniline derivatives has been reported but a cyclization with complete retention of the alkoxycarbonyl group is rare; see: (a) Reference 13a. (b) Reference 15b.
175. II, respectively.
176. Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1999; pp 503-550.