Efficient synthesis of 1-adamantanecarboxaldehyde by the GaCl 3-mediated carbonylation of adamantane under mild reaction conditions

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4323-4325

  Oshita, Masayuki ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE;

ARTICLE; CARBONYLATION; CHEMICAL REACTION; ROOM TEMPERATURE; SYNTHESIS;

EID: 9444264289     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0481636     Document Type: Article

References (23)

1. Bahrmann, H. In New Syntheses with Carbon Monoxide; Falbe, J., Ed.; Springer-Verlag: Berlin, 1980; pp 372-413. Carbonylation; Coloquhoun, H. M., Thomson, D. J., Twigg, M. V., Eds.; Plenum Press: New York, 1991.
2. Bahrmann, H. In New Syntheses with Carbon Monoxide; Falbe, J., Ed.; Springer-Verlag: Berlin, 1980; pp 372-413. Carbonylation; Coloquhoun, H. M., Thomson, D. J., Twigg, M. V., Eds.; Plenum Press: New York, 1991.
3. Yoneda, N.; Takahashi, Y.; Fukuhara, T.; Suzuki, A. Bull. Chem. Soc Jpn 1986, 59, 2819. Delavarenne, S.; Simon, M.; Fauconet, M.; Sommer, J. J. Am. Chem. Soc. 1989, 111, 383. Souma, Y.; Tsumori, N.; Willner, H.; Xu, Q.; Mori, H.; Morisaki, Y. J. Mol. Catal. A 2002, 189, 67 and references therein.
4. Yoneda, N.; Takahashi, Y.; Fukuhara, T.; Suzuki, A. Bull. Chem. Soc Jpn 1986, 59, 2819. Delavarenne, S.; Simon, M.; Fauconet, M.; Sommer, J. J. Am. Chem. Soc. 1989, 111, 383. Souma, Y.; Tsumori, N.; Willner, H.; Xu, Q.; Mori, H.; Morisaki, Y. J. Mol. Catal. A 2002, 189, 67 and references therein.
5. Yoneda, N.; Takahashi, Y.; Fukuhara, T.; Suzuki, A. Bull. Chem. Soc Jpn 1986, 59, 2819. Delavarenne, S.; Simon, M.; Fauconet, M.; Sommer, J. J. Am. Chem. Soc. 1989, 111, 383. Souma, Y.; Tsumori, N.; Willner, H.; Xu, Q.; Mori, H.; Morisaki, Y. J. Mol. Catal. A 2002, 189, 67 and references therein.
6. Takeuchi, K.; Akiyama, F.; Miyazaki, T.; Kitagawa, I.; Okamoto, K. Tetrahedron 1987, 43, 701. Olah, G. A.; Prakash, G. K. S.; Marinez, E. K. Angew. Chem., Int. Ed. 2000, 39, 2547 and references therein.
7. Takeuchi, K.; Akiyama, F.; Miyazaki, T.; Kitagawa, I.; Okamoto, K. Tetrahedron 1987, 43, 701. Olah, G. A.; Prakash, G. K. S.; Marinez, E. K. Angew. Chem., Int. Ed. 2000, 39, 2547 and references therein.
8. Farooq, O.; Marcelli, M.; Prakash, G. K. S.; Olah, G. A. J. Am. Chem. Soc. 1988, 110, 864.
9. Olah, G. A.; Wang, Q. Synthesis 1992, 1090.
10. Akhrem, I.; Churilova, I.; Bernadyuk, S.; Vol'pin, M. Tetrahedron Lett. 1996, 37, 5775. Akhrem, I. S.; Churilova, I. M.; Bernadyuk, S. Z.; Vol'pin, M. E. Russ. Chem. Bull. 1997, 46, 491. Akhrem, I. S. Russ. Chem. Bull. 2003, 52, 2606.
11. Akhrem, I.; Churilova, I.; Bernadyuk, S.; Vol'pin, M. Tetrahedron Lett. 1996, 37, 5775. Akhrem, I. S.; Churilova, I. M.; Bernadyuk, S. Z.; Vol'pin, M. E. Russ. Chem. Bull. 1997, 46, 491. Akhrem, I. S. Russ. Chem. Bull. 2003, 52, 2606.
12. Akhrem, I.; Churilova, I.; Bernadyuk, S.; Vol'pin, M. Tetrahedron Lett. 1996, 37, 5775. Akhrem, I. S.; Churilova, I. M.; Bernadyuk, S. Z.; Vol'pin, M. E. Russ. Chem. Bull. 1997, 46, 491. Akhrem, I. S. Russ. Chem. Bull. 2003, 52, 2606.
13. 3 has been found to show a unique catalytic activity. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553. Amemiya, R.; Fujii, A.; Arisawa, M.; Yamaguchi, M. J. Organomet. Chem. 2003, 686, 94. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991. Chatani, N.; Oshita, M.; Tohisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307. Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333.
14. 3 has been found to show a unique catalytic activity. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553. Amemiya, R.; Fujii, A.; Arisawa, M.; Yamaguchi, M. J. Organomet. Chem. 2003, 686, 94. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991. Chatani, N.; Oshita, M.; Tohisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307. Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333.
15. 3 has been found to show a unique catalytic activity. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553. Amemiya, R.; Fujii, A.; Arisawa, M.; Yamaguchi, M. J. Organomet. Chem. 2003, 686, 94. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991. Chatani, N.; Oshita, M.; Tohisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307. Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333.
16. 3 has been found to show a unique catalytic activity. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553. Amemiya, R.; Fujii, A.; Arisawa, M.; Yamaguchi, M. J. Organomet. Chem. 2003, 686, 94. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991. Chatani, N.; Oshita, M.; Tohisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307. Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333.
17. 3 has been found to show a unique catalytic activity. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553. Amemiya, R.; Fujii, A.; Arisawa, M.; Yamaguchi, M. J. Organomet. Chem. 2003, 686, 94. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991. Chatani, N.; Oshita, M.; Tohisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307. Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333.
18. 3 has been found to show a unique catalytic activity. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553. Amemiya, R.; Fujii, A.; Arisawa, M.; Yamaguchi, M. J. Organomet. Chem. 2003, 686, 94. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991. Chatani, N.; Oshita, M.; Tohisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307. Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333.
19. 3 has been found to show a unique catalytic activity. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553. Amemiya, R.; Fujii, A.; Arisawa, M.; Yamaguchi, M. J. Organomet. Chem. 2003, 686, 94. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991. Chatani, N.; Oshita, M.; Tohisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307. Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333.
20. 3 has been found to show a unique catalytic activity. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553. Amemiya, R.; Fujii, A.; Arisawa, M.; Yamaguchi, M. J. Organomet. Chem. 2003, 686, 94. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991. Chatani, N.; Oshita, M.; Tohisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307. Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333.
21. Yonehara, F.; Kido, Y.; Morita, S.; Yamaguchi, M. J. Am. Chem. Soc. 2001, 123, 11310. Yonehara, F.; Kido, Y.; Sugimoto, H.; Morita, S.; Yamaguchi, M. J. Org. Chem. 2003, 68, 6752.
22. Yonehara, F.; Kido, Y.; Morita, S.; Yamaguchi, M. J. Am. Chem. Soc. 2001, 123, 11310. Yonehara, F.; Kido, Y.; Sugimoto, H.; Morita, S.; Yamaguchi, M. J. Org. Chem. 2003, 68, 6752.
23. +, 2.9), 135 (100), 107 (12), 93 (29), 79 (41), 67 (21), 55 (14).