Ruthenium-catalyzed reaction of α,β-unsaturated imines with carbon monoxide and alkenes leading to β,γ-unsaturated γ-butyrolactams: Involvement of direct carbonylation at olefinic C-H bonds as a key step

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 7014-7018

  Chatani, Naoto ^a   Kamitani, Akihito ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOPHILIC ATTACKS;

CATALYSIS; CATALYSTS; CHEMICAL BONDS; KETONES; OLEFINS; RUTHENIUM;

CARBONYLATION;

2 PYRROLIDONE DERIVATIVE; ALKENE; CARBON; CARBON MONOXIDE; CARBONYL DERIVATIVE; HYDROGEN; IMINE; KETONE; RUTHENIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037020009     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026001m     Document Type: Article

References (44)

1. For reviews on carbonylation reactions, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Kühlein, K.; Geissler, H. In Transition Metal for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998, pp 79-90. Cornis, B., Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, Germany, 1996, Vol. 1. Nozaki, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, Vol. 1, pp 381-413. Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. Bertoux, F.; Monflier, E.; Castanet, Y.; Mortreux, A. J. Mol. Catal. A 1999, 143, 11. El Ali, B.; Alper, H. Synlett 2000, 161. Kiss, G. Chem. Rev. 2001, 101, 3435.
2. For reviews on carbonylation reactions, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Kühlein, K.; Geissler, H. In Transition Metal for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998, pp 79-90. Cornis, B., Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, Germany, 1996, Vol. 1. Nozaki, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, Vol. 1, pp 381-413. Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. Bertoux, F.; Monflier, E.; Castanet, Y.; Mortreux, A. J. Mol. Catal. A 1999, 143, 11. El Ali, B.; Alper, H. Synlett 2000, 161. Kiss, G. Chem. Rev. 2001, 101, 3435.
3. For reviews on carbonylation reactions, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Kühlein, K.; Geissler, H. In Transition Metal for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998, pp 79-90. Cornis, B., Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, Germany, 1996, Vol. 1. Nozaki, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, Vol. 1, pp 381-413. Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. Bertoux, F.; Monflier, E.; Castanet, Y.; Mortreux, A. J. Mol. Catal. A 1999, 143, 11. El Ali, B.; Alper, H. Synlett 2000, 161. Kiss, G. Chem. Rev. 2001, 101, 3435.
4. For reviews on carbonylation reactions, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Kühlein, K.; Geissler, H. In Transition Metal for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998, pp 79-90. Cornis, B., Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, Germany, 1996, Vol. 1. Nozaki, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, Vol. 1, pp 381-413. Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. Bertoux, F.; Monflier, E.; Castanet, Y.; Mortreux, A. J. Mol. Catal. A 1999, 143, 11. El Ali, B.; Alper, H. Synlett 2000, 161. Kiss, G. Chem. Rev. 2001, 101, 3435.
5. For reviews on carbonylation reactions, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Kühlein, K.; Geissler, H. In Transition Metal for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998, pp 79-90. Cornis, B., Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, Germany, 1996, Vol. 1. Nozaki, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, Vol. 1, pp 381-413. Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. Bertoux, F.; Monflier, E.; Castanet, Y.; Mortreux, A. J. Mol. Catal. A 1999, 143, 11. El Ali, B.; Alper, H. Synlett 2000, 161. Kiss, G. Chem. Rev. 2001, 101, 3435.
6. For reviews on carbonylation reactions, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Kühlein, K.; Geissler, H. In Transition Metal for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998, pp 79-90. Cornis, B., Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, Germany, 1996, Vol. 1. Nozaki, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, Vol. 1, pp 381-413. Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. Bertoux, F.; Monflier, E.; Castanet, Y.; Mortreux, A. J. Mol. Catal. A 1999, 143, 11. El Ali, B.; Alper, H. Synlett 2000, 161. Kiss, G. Chem. Rev. 2001, 101, 3435.
7. For reviews on carbonylation reactions, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Kühlein, K.; Geissler, H. In Transition Metal for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998, pp 79-90. Cornis, B., Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, Germany, 1996, Vol. 1. Nozaki, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, Vol. 1, pp 381-413. Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. Bertoux, F.; Monflier, E.; Castanet, Y.; Mortreux, A. J. Mol. Catal. A 1999, 143, 11. El Ali, B.; Alper, H. Synlett 2000, 161. Kiss, G. Chem. Rev. 2001, 101, 3435.
8. For reviews on carbonylation reactions, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Kühlein, K.; Geissler, H. In Transition Metal for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998, pp 79-90. Cornis, B., Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, Germany, 1996, Vol. 1. Nozaki, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, Vol. 1, pp 381-413. Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. Bertoux, F.; Monflier, E.; Castanet, Y.; Mortreux, A. J. Mol. Catal. A 1999, 143, 11. El Ali, B.; Alper, H. Synlett 2000, 161. Kiss, G. Chem. Rev. 2001, 101, 3435.
9. For our recent papers on carbonylative cycloaddition reactions, see: (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (c) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177. (d) Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160. (e) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. (f) Chatani, N.; Tobisu, M.; Asaumi, T.; Murai, S. Synthesis 2000, 925. (g) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, Y.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (h) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230. (i) Chatani, N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686.
10. For our recent papers on carbonylative cycloaddition reactions, see: (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (c) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177. (d) Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160. (e) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. (f) Chatani, N.; Tobisu, M.; Asaumi, T.; Murai, S. Synthesis 2000, 925. (g) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, Y.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (h) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230. (i) Chatani, N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686.
11. For our recent papers on carbonylative cycloaddition reactions, see: (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (c) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177. (d) Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160. (e) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. (f) Chatani, N.; Tobisu, M.; Asaumi, T.; Murai, S. Synthesis 2000, 925. (g) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, Y.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (h) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230. (i) Chatani, N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686.
12. For our recent papers on carbonylative cycloaddition reactions, see: (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (c) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177. (d) Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160. (e) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. (f) Chatani, N.; Tobisu, M.; Asaumi, T.; Murai, S. Synthesis 2000, 925. (g) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, Y.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (h) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230. (i) Chatani, N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686.
13. For our recent papers on carbonylative cycloaddition reactions, see: (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (c) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177. (d) Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160. (e) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. (f) Chatani, N.; Tobisu, M.; Asaumi, T.; Murai, S. Synthesis 2000, 925. (g) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, Y.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (h) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230. (i) Chatani, N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686.
14. For our recent papers on carbonylative cycloaddition reactions, see: (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (c) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177. (d) Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160. (e) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. (f) Chatani, N.; Tobisu, M.; Asaumi, T.; Murai, S. Synthesis 2000, 925. (g) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, Y.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (h) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230. (i) Chatani, N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686.
15. For our recent papers on carbonylative cycloaddition reactions, see: (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (c) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177. (d) Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160. (e) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. (f) Chatani, N.; Tobisu, M.; Asaumi, T.; Murai, S. Synthesis 2000, 925. (g) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, Y.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (h) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230. (i) Chatani, N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686.
16. For our recent papers on carbonylative cycloaddition reactions, see: (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (c) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177. (d) Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160. (e) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. (f) Chatani, N.; Tobisu, M.; Asaumi, T.; Murai, S. Synthesis 2000, 925. (g) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, Y.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (h) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230. (i) Chatani, N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686.
17. For our recent papers on carbonylative cycloaddition reactions, see: (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (c) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177. (d) Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160. (e) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758. (f) Chatani, N.; Tobisu, M.; Asaumi, T.; Murai, S. Synthesis 2000, 925. (g) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, Y.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (h) Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230. (i) Chatani, N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686.
18. For our recent papers on direct carbonylation at C-H bonds, see: (a) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (b) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604. (c) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647. (d) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129. (e) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522. (f) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475. (g) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039. (h) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
19. For our recent papers on direct carbonylation at C-H bonds, see: (a) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (b) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604. (c) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647. (d) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129. (e) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522. (f) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475. (g) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039. (h) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
20. For our recent papers on direct carbonylation at C-H bonds, see: (a) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (b) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604. (c) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647. (d) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129. (e) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522. (f) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475. (g) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039. (h) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
21. For our recent papers on direct carbonylation at C-H bonds, see: (a) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (b) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604. (c) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647. (d) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129. (e) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522. (f) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475. (g) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039. (h) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
22. For our recent papers on direct carbonylation at C-H bonds, see: (a) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (b) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604. (c) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647. (d) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129. (e) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522. (f) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475. (g) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039. (h) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
23. For our recent papers on direct carbonylation at C-H bonds, see: (a) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (b) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604. (c) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647. (d) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129. (e) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522. (f) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475. (g) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039. (h) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
24. For our recent papers on direct carbonylation at C-H bonds, see: (a) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (b) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604. (c) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647. (d) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129. (e) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522. (f) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475. (g) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039. (h) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
25. For our recent papers on direct carbonylation at C-H bonds, see: (a) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (b) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604. (c) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647. (d) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129. (e) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522. (f) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475. (g) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039. (h) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
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30. All new compounds were characterized by NMR, IR, mass spectral data, and either elemental analyses or high-resolution mass spectra. For detailed data, see Supporting Information.
31. These experimental results are consistent with a direct carbonylation at the ortho C-H bonds in the present reaction. In all carbonylation reactions at ortho C-H bonds reported thus far, hexene was found to be unreactive. See refs 3b, 3c, and 3f.
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