Indole synthesis via palladium-catalyzed intramolecular cyclization of alkynes and imines [14]

Journal of the American Chemical Society

Volumn 122, Issue 23, 2000, Pages 5662-5663

  Takeda, Akira ^a   Kamijo, Shin ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; FUNCTIONAL GROUP; IMINE; INDOLE; PALLADIUM;

AMINO TERMINAL SEQUENCE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034647204     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000390p     Document Type: Letter

References (36)

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2. (a) For reviews, see: Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (b) Colquhoun, H. M.; Holston, J.; Thompson, D. J.; Twigg, M. V. New Pathway for Organic Synthesis: Practical Applications of Transition Metals; Plenum Press: New York, 1984; p 148. (c) Sakamoto, T.; Kondo, Y.; Hiroshi, Y. Heterocycles 1988, 27, 2225.
3. (a) For reviews, see: Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (b) Colquhoun, H. M.; Holston, J.; Thompson, D. J.; Twigg, M. V. New Pathway for Organic Synthesis: Practical Applications of Transition Metals; Plenum Press: New York, 1984; p 148. (c) Sakamoto, T.; Kondo, Y.; Hiroshi, Y. Heterocycles 1988, 27, 2225.
4. (a) For reviews, see: Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (b) Colquhoun, H. M.; Holston, J.; Thompson, D. J.; Twigg, M. V. New Pathway for Organic Synthesis: Practical Applications of Transition Metals; Plenum Press: New York, 1984; p 148. (c) Sakamoto, T.; Kondo, Y.; Hiroshi, Y. Heterocycles 1988, 27, 2225.
5. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
6. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
7. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
8. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
9. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
10. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
11. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
12. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
13. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
14. 2-Alkynylanilines: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963. (b) Iritani, K.; Matsubara, S. Utimoto, K. Tetrahedron Lett. 1988, 29, 1799. (c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. (d) Kondo, Y.; N. Shiga.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. N-Allyl-2-haloanilines: (e) Larock, R. C.; Basu, S. Tetrahedron Lett. 1987, 28, 5291. N-Vinyl-2-haloanilines: (f) Kasahara, A.; Szumi, T.; Murakami, S.; Yanai, H.; Takatori, M.; Bull. Chem. Soc. Jpn. 1986, 59, 927. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. Intermolecular cycloaddition of 2-haloanilines and alkynes: (h) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. (i) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. (j) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
15. For the C-2-C-3 bond formation via radical cyclization: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (b) Tokuyama, H.; Yamashita, T.; Reding, M. T.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 1999, 121, 3791. (c) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325.
16. For the C-2-C-3 bond formation via radical cyclization: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (b) Tokuyama, H.; Yamashita, T.; Reding, M. T.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 1999, 121, 3791. (c) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325.
17. For the C-2-C-3 bond formation via radical cyclization: (a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127. (b) Tokuyama, H.; Yamashita, T.; Reding, M. T.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 1999, 121, 3791. (c) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325.
18. (a) Bergamasco, R.; Porter, Q. N.; Yap, C. Aust. J. Chem. 1977, 30, 1531.
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20. (c) Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K., 1984; Vol. 4, p 282.
21. 4, and Dean-Stark dehydrator was very sluggish and not completed even after a prolonged reaction time. However, the use of molecular sieves gave 1a-i in high yields with shorter reaction times. In the case of aliphatic aldehydes, there was no need to use molecular sieves: (a) Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic Press: Orlando, FL, 1986; Chapter 12. (b) Layer, R. B. Chem. Rev. 1963, 63, 489.
22. 4, and Dean-Stark dehydrator was very sluggish and not completed even after a prolonged reaction time. However, the use of molecular sieves gave 1a-i in high yields with shorter reaction times. In the case of aliphatic aldehydes, there was no need to use molecular sieves: (a) Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic Press: Orlando, FL, 1986; Chapter 12. (b) Layer, R. B. Chem. Rev. 1963, 63, 489.
23. For a recent review for C-H bond activation, see: (a) Gerald, D. Angew. Chem., Int. Ed. 1999, 38, 1698. Oxidative addition of aldehyde's C-H bond to a transition metal complexes: (b) Barnhart, R. W.; McMorran, D. A.; Bosnich, B. Chem. Commun. 1997, 589. (c) Kokubo, K.; Matsubara, K.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4564. (d) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165. (e) Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286.
24. For a recent review for C-H bond activation, see: (a) Gerald, D. Angew. Chem., Int. Ed. 1999, 38, 1698. Oxidative addition of aldehyde's C-H bond to a transition metal complexes: (b) Barnhart, R. W.; McMorran, D. A.; Bosnich, B. Chem. Commun. 1997, 589. (c) Kokubo, K.; Matsubara, K.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4564. (d) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165. (e) Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286.
25. For a recent review for C-H bond activation, see: (a) Gerald, D. Angew. Chem., Int. Ed. 1999, 38, 1698. Oxidative addition of aldehyde's C-H bond to a transition metal complexes: (b) Barnhart, R. W.; McMorran, D. A.; Bosnich, B. Chem. Commun. 1997, 589. (c) Kokubo, K.; Matsubara, K.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4564. (d) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165. (e) Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286.
26. For a recent review for C-H bond activation, see: (a) Gerald, D. Angew. Chem., Int. Ed. 1999, 38, 1698. Oxidative addition of aldehyde's C-H bond to a transition metal complexes: (b) Barnhart, R. W.; McMorran, D. A.; Bosnich, B. Chem. Commun. 1997, 589. (c) Kokubo, K.; Matsubara, K.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4564. (d) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165. (e) Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286.
27. For a recent review for C-H bond activation, see: (a) Gerald, D. Angew. Chem., Int. Ed. 1999, 38, 1698. Oxidative addition of aldehyde's C-H bond to a transition metal complexes: (b) Barnhart, R. W.; McMorran, D. A.; Bosnich, B. Chem. Commun. 1997, 589. (c) Kokubo, K.; Matsubara, K.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4564. (d) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165. (e) Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286.
28. No deuterium was found in the other carbons of the indole product.
29. The intramolecular cyclization of vinylpalladium and aldehydes or ketones, see: (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545. (b) Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089. (c) Tao, W.; Silverberg, L. J.; Rheingold, A. L.; Heck, R. F. Organometallics 1989, 8, 2550. (d) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org.Chem. 1993, 58, 4579. For the intramolecular cyclization of vinylpalladium and imines, see ref 3j.
30. The intramolecular cyclization of vinylpalladium and aldehydes or ketones, see: (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545. (b) Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089. (c) Tao, W.; Silverberg, L. J.; Rheingold, A. L.; Heck, R. F. Organometallics 1989, 8, 2550. (d) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org.Chem. 1993, 58, 4579. For the intramolecular cyclization of vinylpalladium and imines, see ref 3j.
31. The intramolecular cyclization of vinylpalladium and aldehydes or ketones, see: (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545. (b) Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089. (c) Tao, W.; Silverberg, L. J.; Rheingold, A. L.; Heck, R. F. Organometallics 1989, 8, 2550. (d) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org.Chem. 1993, 58, 4579. For the intramolecular cyclization of vinylpalladium and imines, see ref 3j.
32. The intramolecular cyclization of vinylpalladium and aldehydes or ketones, see: (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545. (b) Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089. (c) Tao, W.; Silverberg, L. J.; Rheingold, A. L.; Heck, R. F. Organometallics 1989, 8, 2550. (d) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org.Chem. 1993, 58, 4579. For the intramolecular cyclization of vinylpalladium and imines, see ref 3j.
33. Mandai, T.; Matsumoto, T.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1993, 34, 2513.
34. (a) For a review, see: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Trost, B. M.; Lee, D. C.; Rise, F. Tetrahedron Lett. 1989, 30, 651.
35. (a) For a review, see: Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Trost, B. M.; Lee, D. C.; Rise, F. Tetrahedron Lett. 1989, 30, 651.
36. 2O exist in the reaction media, although a dry solvent was used.