Synthesis of a Novel C2-Symmetric Thiourea and Its Application in the Pd-Catalyzed Cross-Coupling Reactions with Arenediazonium Salts under Aerobic Conditions

Organic Letters

Volumn 6, Issue 2, 2004, Pages 221-224

  Dai, Mingji ^a   Liang, Bo ^a   Wang, Cuihua ^a   Chen, Jiahua ^a   Yang, Zhen ^a,b  

^a PEKING UNIVERSITY   (China)

^b VivoQuest Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; BASE; DIAZONIUM COMPOUND; LIGAND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOUREA DERIVATIVE;

AEROBIC METABOLISM; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; HECK REACTION; ROOM TEMPERATURE; SUZUKI REACTION;

EID: 0842325286     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036182u     Document Type: Article

References (93)

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12. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
13. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
14. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
15. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
16. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
17. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
18. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
19. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
20. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
21. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
22. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
23. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
24. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
25. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
26. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
27. For Heck reaction with arenediazonium salt, see: (a) Kikukawa, K.; Nagira, K.; Terao, N.; Wada, F.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 2609. (b) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359. (c) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.(d) Kikukawa, K.; Maemura, K.; Kiseki, Y.; Wada, F.; Matsudo, T. Giam, C. S. J. Org. Chem. 1981, 46, 4885. (e) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1986, 1959. (f) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873. (g) Wang, Y.; Pang, Y.; Zhang, Z.; Hu, H. Synthesis 1991, 967. (h) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943. (i) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773. (j) Beller, M.; Kühlein, K. Synlett 1995, 441. (k) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213. (l) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407. (m) Colas, C.; Goelder, M. Eur. J. Org. Chem. 1999, 1357. (n) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 4815. (o) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (p) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079. (q) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
28. For Suzuki reaction with arenediazonium salt, see: (r) Darses, S.; Jeffery, T.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1996, 37, 3857. (s) Darses, S.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1997, 38, 4393. (t) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (u) Darses, S.; Michaud, G.; Genêt. J.-P. Eur. J. Org. Chem. 1999, 1875. (v) Willis, D. M.; Strongin, R. M. Tetrahedron Lett. 2000, 41, 6271. (w) Andrus, M. B., Song, C. Org. Lett. 2001, 3, 3761.
29. For Suzuki reaction with arenediazonium salt, see: (r) Darses, S.; Jeffery, T.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1996, 37, 3857. (s) Darses, S.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1997, 38, 4393. (t) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (u) Darses, S.; Michaud, G.; Genêt. J.-P. Eur. J. Org. Chem. 1999, 1875. (v) Willis, D. M.; Strongin, R. M. Tetrahedron Lett. 2000, 41, 6271. (w) Andrus, M. B., Song, C. Org. Lett. 2001, 3, 3761.
30. For Suzuki reaction with arenediazonium salt, see: (r) Darses, S.; Jeffery, T.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1996, 37, 3857. (s) Darses, S.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1997, 38, 4393. (t) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (u) Darses, S.; Michaud, G.; Genêt. J.-P. Eur. J. Org. Chem. 1999, 1875. (v) Willis, D. M.; Strongin, R. M. Tetrahedron Lett. 2000, 41, 6271. (w) Andrus, M. B., Song, C. Org. Lett. 2001, 3, 3761.
31. For Suzuki reaction with arenediazonium salt, see: (r) Darses, S.; Jeffery, T.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1996, 37, 3857. (s) Darses, S.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1997, 38, 4393. (t) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (u) Darses, S.; Michaud, G.; Genêt. J.-P. Eur. J. Org. Chem. 1999, 1875. (v) Willis, D. M.; Strongin, R. M. Tetrahedron Lett. 2000, 41, 6271. (w) Andrus, M. B., Song, C. Org. Lett. 2001, 3, 3761.
32. For Suzuki reaction with arenediazonium salt, see: (r) Darses, S.; Jeffery, T.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1996, 37, 3857. (s) Darses, S.; Genêt, J.-P.; Brayer, J.-L,; Demoute, J.-P. Tetrahedron Lett. 1997, 38, 4393. (t) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (u) Darses, S.; Michaud, G.; Genêt. J.-P. Eur. J. Org. Chem. 1999, 1875. (v) Willis, D. M.; Strongin, R. M. Tetrahedron Lett. 2000, 41, 6271. (w) Andrus, M. B., Song, C. Org. Lett. 2001, 3, 3761.
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92. 4 see Supporting Information for detail.
93. 2 (0.005 mmol), ligand 3 (0.005 mmol), olefin or arylboronic acid (0.6 mmol), and arenediazonium tetrafluoroborate salt (0.5 mmol) were mixed in methanol (5.0 mL), and the reaction mixture was stirred at room temperature for 4 h under aerobic conditions. The reaction was worked up by removing the solvent under vacuum, and the residue was purified by chromatography on silica gel.