Rhenium(I)-catalyzed intramolecular geminal carbofunctionalization of alkynes: Tandem cyclization of ω-acetylenic dienol silyl ethers

Angewandte Chemie - International Edition

Volumn 44, Issue 3, 2005, Pages 468-470

  Kusama, Hiroyuki ^a   Yamabe, Hokuto ^a   Onizawa, Yuji ^a   Hoshino, Takahiko ^a   Iwasawa, Nobuharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkynes; Cyclization; Homogeneous catalysis; Rhenium; Silyl ethers

Indexed keywords

CATALYSIS; COMPLEXATION; ETHERS; IRRADIATION; REACTION KINETICS; RHENIUM;

ALKYNES; GEMINAL CARBOFUNCTIONALIZATION; PHOTOIRRADIATION; TANDEM INTRAMOLECULAR CYCLIZATION;

CATALYST ACTIVITY;

ACETYLENE; ALKYNE; CARBON; RHENIUM; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CYCLIZATION; ELECTROPHORESIS; MOLECULE; REACTION ANALYSIS;

ACETYLENE; ALKYNES; CATALYSIS; CYCLIZATION; ETHERS; RHENIUM;

EID: 12344316230     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461559     Document Type: Article

References (40)

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2. For reviews on carbometalation, see: a) I. Marek, J. F. Normant in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1997, p. 271; b) W. Oppolzer, Angew. Chem. 1989, 101, 39; Angew. Chem. Int. Ed. Engl. 1989, 28, 38; c) E. Negishi, Chem. Eur. J. 1999, 5, 411.
3. For reviews on carbometalation, see: a) I. Marek, J. F. Normant in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1997, p. 271; b) W. Oppolzer, Angew. Chem. 1989, 101, 39; Angew. Chem. Int. Ed. Engl. 1989, 28, 38; c) E. Negishi, Chem. Eur. J. 1999, 5, 411.
4. For reviews on carbometalation, see: a) I. Marek, J. F. Normant in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1997, p. 271; b) W. Oppolzer, Angew. Chem. 1989, 101, 39; Angew. Chem. Int. Ed. Engl. 1989, 28, 38; c) E. Negishi, Chem. Eur. J. 1999, 5, 411.
5. To the best of our knowledge, the geminal carbofunctionalization reactions previously reported have been confined to cyclopropanations to generate cyclopropyl carbene complexes, see: a) N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104; b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863, and references therein; c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511; d) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456; Angew. Chem. Int. Ed. 2004, 43, 2402; e) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654; f) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656; g) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524; h) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858.
6. To the best of our knowledge, the geminal carbofunctionalization reactions previously reported have been confined to cyclopropanations to generate cyclopropyl carbene complexes, see: a) N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104; b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863, and references therein; c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511; d) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456; Angew. Chem. Int. Ed. 2004, 43, 2402; e) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654; f) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656; g) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524; h) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858.
7. To the best of our knowledge, the geminal carbofunctionalization reactions previously reported have been confined to cyclopropanations to generate cyclopropyl carbene complexes, see: a) N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104; b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863, and references therein; c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511; d) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456; Angew. Chem. Int. Ed. 2004, 43, 2402; e) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654; f) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656; g) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524; h) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858.
8. To the best of our knowledge, the geminal carbofunctionalization reactions previously reported have been confined to cyclopropanations to generate cyclopropyl carbene complexes, see: a) N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104; b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863, and references therein; c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511; d) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456; Angew. Chem. Int. Ed. 2004, 43, 2402; e) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654; f) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656; g) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524; h) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858.
9. To the best of our knowledge, the geminal carbofunctionalization reactions previously reported have been confined to cyclopropanations to generate cyclopropyl carbene complexes, see: a) N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104; b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863, and references therein; c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511; d) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456; Angew. Chem. Int. Ed. 2004, 43, 2402; e) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654; f) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656; g) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524; h) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858.
10. To the best of our knowledge, the geminal carbofunctionalization reactions previously reported have been confined to cyclopropanations to generate cyclopropyl carbene complexes, see: a) N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104; b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863, and references therein; c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511; d) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456; Angew. Chem. Int. Ed. 2004, 43, 2402; e) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654; f) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656; g) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524; h) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858.
11. To the best of our knowledge, the geminal carbofunctionalization reactions previously reported have been confined to cyclopropanations to generate cyclopropyl carbene complexes, see: a) N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104; b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863, and references therein; c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511; d) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456; Angew. Chem. Int. Ed. 2004, 43, 2402; e) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654; f) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656; g) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524; h) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858.
12. To the best of our knowledge, the geminal carbofunctionalization reactions previously reported have been confined to cyclopropanations to generate cyclopropyl carbene complexes, see: a) N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104; b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863, and references therein; c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511; d) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456; Angew. Chem. Int. Ed. 2004, 43, 2402; e) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654; f) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656; g) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524; h) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858.
13. To the best of our knowledge, the geminal carbofunctionalization reactions previously reported have been confined to cyclopropanations to generate cyclopropyl carbene complexes, see: a) N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104; b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863, and references therein; c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511; d) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456; Angew. Chem. Int. Ed. 2004, 43, 2402; e) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654; f) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656; g) B. P. Peppers, S. T. Diver, J. Am. Chem. Soc. 2004, 126, 9524; h) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858.
14. For examples of geminal functionalization of alkynes involving heteroatom-carbon bond formation, see: a) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814; b) H. Kusama, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 11592; c) J. Takaya, H. Kusama, N. Iwasawa, Chem. Lett. 2004, 33, 16; d) F. Nishino, K. Miki, Y. Kato, K. Ohe, S. Uemura, Org. Lett. 2003, 5, 2615; e) K. Miki, K. Ohe, S. Uemura, J. Org. Chem. 2003, 68, 8505; f) K. Miki, T. Yokoi, F. Nishino, Y. Kato, Y. Washitake, K. Ohe, S. Uemura, J. Org. Chem. 2004, 69, 1557.
15. For examples of geminal functionalization of alkynes involving heteroatom-carbon bond formation, see: a) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814; b) H. Kusama, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 11592; c) J. Takaya, H. Kusama, N. Iwasawa, Chem. Lett. 2004, 33, 16; d) F. Nishino, K. Miki, Y. Kato, K. Ohe, S. Uemura, Org. Lett. 2003, 5, 2615; e) K. Miki, K. Ohe, S. Uemura, J. Org. Chem. 2003, 68, 8505; f) K. Miki, T. Yokoi, F. Nishino, Y. Kato, Y. Washitake, K. Ohe, S. Uemura, J. Org. Chem. 2004, 69, 1557.
16. For examples of geminal functionalization of alkynes involving heteroatom-carbon bond formation, see: a) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814; b) H. Kusama, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 11592; c) J. Takaya, H. Kusama, N. Iwasawa, Chem. Lett. 2004, 33, 16; d) F. Nishino, K. Miki, Y. Kato, K. Ohe, S. Uemura, Org. Lett. 2003, 5, 2615; e) K. Miki, K. Ohe, S. Uemura, J. Org. Chem. 2003, 68, 8505; f) K. Miki, T. Yokoi, F. Nishino, Y. Kato, Y. Washitake, K. Ohe, S. Uemura, J. Org. Chem. 2004, 69, 1557.
17. For examples of geminal functionalization of alkynes involving heteroatom-carbon bond formation, see: a) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814; b) H. Kusama, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 11592; c) J. Takaya, H. Kusama, N. Iwasawa, Chem. Lett. 2004, 33, 16; d) F. Nishino, K. Miki, Y. Kato, K. Ohe, S. Uemura, Org. Lett. 2003, 5, 2615; e) K. Miki, K. Ohe, S. Uemura, J. Org. Chem. 2003, 68, 8505; f) K. Miki, T. Yokoi, F. Nishino, Y. Kato, Y. Washitake, K. Ohe, S. Uemura, J. Org. Chem. 2004, 69, 1557.
18. For examples of geminal functionalization of alkynes involving heteroatom-carbon bond formation, see: a) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814; b) H. Kusama, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 11592; c) J. Takaya, H. Kusama, N. Iwasawa, Chem. Lett. 2004, 33, 16; d) F. Nishino, K. Miki, Y. Kato, K. Ohe, S. Uemura, Org. Lett. 2003, 5, 2615; e) K. Miki, K. Ohe, S. Uemura, J. Org. Chem. 2003, 68, 8505; f) K. Miki, T. Yokoi, F. Nishino, Y. Kato, Y. Washitake, K. Ohe, S. Uemura, J. Org. Chem. 2004, 69, 1557.
19. For examples of geminal functionalization of alkynes involving heteroatom-carbon bond formation, see: a) N. Iwasawa, M. Shido, H. Kusama, J. Am. Chem. Soc. 2001, 123, 5814; b) H. Kusama, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 11592; c) J. Takaya, H. Kusama, N. Iwasawa, Chem. Lett. 2004, 33, 16; d) F. Nishino, K. Miki, Y. Kato, K. Ohe, S. Uemura, Org. Lett. 2003, 5, 2615; e) K. Miki, K. Ohe, S. Uemura, J. Org. Chem. 2003, 68, 8505; f) K. Miki, T. Yokoi, F. Nishino, Y. Kato, Y. Washitake, K. Ohe, S. Uemura, J. Org. Chem. 2004, 69, 1557.
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25. For examples of the reaction of Group VI alkenyl metallic species with carbo-electrophiles, see; a) W. D. Wulff, S. R. Gilbertson, J. Am. Chem. Soc, 1985, 107, 503; b) Y.-C. Xu, W. D. Wulff, J. Org. Chem. 1987, 52, 3263; c) R. Aumann, H. Heinen, Chem. Ber. 1987, 120, 537; d) B. A. Anderson, W. D. Wulff, A. Rahm, J. Am. Chem. Soc. 1993, 115, 4602.
26. For examples of the reaction of Group VI alkenyl metallic species with carbo-electrophiles, see; a) W. D. Wulff, S. R. Gilbertson, J. Am. Chem. Soc, 1985, 107, 503; b) Y.-C. Xu, W. D. Wulff, J. Org. Chem. 1987, 52, 3263; c) R. Aumann, H. Heinen, Chem. Ber. 1987, 120, 537; d) B. A. Anderson, W. D. Wulff, A. Rahm, J. Am. Chem. Soc. 1993, 115, 4602.
27. For examples of the reaction of Group VI alkenyl metallic species with carbo-electrophiles, see; a) W. D. Wulff, S. R. Gilbertson, J. Am. Chem. Soc, 1985, 107, 503; b) Y.-C. Xu, W. D. Wulff, J. Org. Chem. 1987, 52, 3263; c) R. Aumann, H. Heinen, Chem. Ber. 1987, 120, 537; d) B. A. Anderson, W. D. Wulff, A. Rahm, J. Am. Chem. Soc. 1993, 115, 4602.
28. Non-heteroatom-substituted alkyl carbene complexes, especially those having an α-hydrogen atom, are highly reactive to give 1,2-hydrogen migration products, see: a) C. P. Casey, L. D. Albin, T. J. Burkhardt, J. Am. Chem. Soc. 1977, 99, 2533; b) J. Barluenga, A. Ballesteros, R. de la R. Bernardo, J. Santamaría, E. Rubio, M. Tomás, J. Am. Chem. Soc. 2003, 125, 1834.
29. Non-heteroatom-substituted alkyl carbene complexes, especially those having an α-hydrogen atom, are highly reactive to give 1,2-hydrogen migration products, see: a) C. P. Casey, L. D. Albin, T. J. Burkhardt, J. Am. Chem. Soc. 1977, 99, 2533; b) J. Barluenga, A. Ballesteros, R. de la R. Bernardo, J. Santamaría, E. Rubio, M. Tomás, J. Am. Chem. Soc. 2003, 125, 1834.
30. [4a]
31. The tricyclic enol silyl ether 3 was not obtained when the substrates without a gera-diester (1b-i) were employed.
32. 6] under photoirradiation in toluene proceeded to only a small extent after 16 h to give < 5 % of cyclized product 2a.
33. 4(L)] is the active species in this reaction.
34. The geometry of the major isomer is shown in the scheme; see the Supporting Information for details of the isomeric ratio of the starting materials.
35. 6] gave 2g in 79 % yield).
36. 3(dppm)]-catalyzed C-C bond-forming reactions (dppm = bis(diphenylphosphanyl)methane), see: d) M. R. Luzung, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 15760.
37. 3(dppm)]-catalyzed C-C bond-forming reactions (dppm = bis(diphenylphosphanyl)methane), see: d) M. R. Luzung, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 15760.
38. 3(dppm)]-catalyzed C-C bond-forming reactions (dppm = bis(diphenylphosphanyl)methane), see: d) M. R. Luzung, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 15760.
39. 3(dppm)]-catalyzed C-C bond-forming reactions (dppm = bis(diphenylphosphanyl)methane), see: d) M. R. Luzung, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 15760.
40. 5]-catalyzed additions of carboxylic acids to terminal alkynes, see: R. Hua, X. Tian, J. Org. Chem. 2004, 69, 5782.