Designing a catalytic synthesis of 4-methylcoumarin from ortho-iodophenyl 3-butenoate: Ring closure and isomerization control

Journal of Organometallic Chemistry

Volumn 525, Issue 1-2, 1996, Pages 65-69

  Catellani, Marta ^a   Chiusoli, Gian Paolo ^a   Marzolini, Giovanna ^a   Rossi, Emanuela ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

Catalysis; Coumarin; Cyclization; Palladium

Indexed keywords

EID: 0030588837     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(96)06489-3     Document Type: Article

References (41)

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5. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
6. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
7. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
8. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
9. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
10. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
11. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
12. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
13. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
14. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
15. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
16. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
17. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
18. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
19. [2] D.R. Fahey and J.E. Mahan, J. Mol. Catal., 3 (1978) 447; R.C. Larock and B.E. Baker, Tetrahedron Lett., 29 (1988) 905; R.C. Larock, H. Song, B.E. Baker and W.H. Gong, Tetrahedron Lett., 29 (1988) 4325; R.C. Larock and D.E. Stinn, Tetrahedron Lett., 29 (1988) 4687; W. Oppolzer, T.H. Keller, M. Bedoya-Zurita and C. Stone, Tetrahedron Lett., 30 (1989) 5883; B. Morin-Phelippeau, A. Favre-Fafet, F. Hugues, D. Commereuc and Y. Chauvin, J. Mol. Catal., 51 (1989) 145; E. Negishi, Y. Zhang, I. Shimoyama and G. Wu, J. Am. Chem. Soc., 111 (1989) 8018; Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29 (1989) 1013; R.C. Larock, N.G. Berrios-Peña and C.A. Fried, J. Org. Chem., 56 (1991) 2615; P.G. Ciattini, E. Morera, G. Ortar and S. Strano Rossi, Tetrahedron, 47 (1991) 6449; S. Tori, H. Okumoto and L. He Xu, Tetrahedron Lett., 32 (1991) 237; V.H. Kalinin, M.V. Shostakovsky and A.B. Ponomaryov, Tetrahedron Lett., 33 (1992) 373; E.I. Neghishi, Pure Appl. Chem., 64 (1992) 323; R. Grigg and V. Sridharan, Tetrahedron Lett., 34 (1993) 7471; S. Tori, H. Okumoto, L. He Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.H. Kalinin, Tetrahedron, 49 (1993) 6773; E.I. Neghishi, C. Copéret, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J.M. Tour, Tetrahedron, 50 (1994) 425; K. Samizu and K. Ogasawara, Synlett, (1994) 499; C.-C. Yang, P.-J. Sun and J.-M. Fang, J. Chem. Soc., Chem. Commun., (1994) 2629; R. Grigg, J. Redpath, V. Sridharan and D. Wilson, Tetrahedron Lett., 35 (1994) 7661; R. Grigg, H. Khalil, P. Levett, J. Virica and V. Sridharan, Tetrahedron Lett., 35 (1994) 3197; R. Grigg, V. Sridharan, S. Suganthan and W. Bridge, Tetrahedron, 51 (1995) 295; S. Brown, S. Clarkson, R. Grigg and V. Sridharan, J. Chem. Soc., Chem. Commun., (1995) 1135.
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