A general procedure to selectively prepare N-alkylanilines by an unexpected reaction of (Z)-(tert-butylsulfanyl)(aryl)diazenes with alkyllithium reagents

Synthesis

Volumn , Issue 5, 2003, Pages 742-750

  Barbero, Margherita ^a   Degani, Iacopo ^a   Dughera, Stefano ^a   Fochi, Rita ^a  

^a Università   (Italy)

Author keywords

Allkyllithium; Amines; Diazonium compounds; Diazosulfides; N alkylanilines

Indexed keywords

CONTAMINATION; ETHERS; SYNTHESIS (CHEMICAL);

OPTIMAL CONDITIONS;

AROMATIC HYDROCARBONS;

ANILINE DERIVATIVE; LITHIUM;

ALKYLATION; ANALYTIC METHOD; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; CONTAMINATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037253096     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38082     Document Type: Article

References (59)

1. Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.; Fochi, R.; Migliaccio, M. J. Org. Chem. 2000, 65, 5600.
2. For some examples on the preparation, stability and synthetic applications of (Z)-(tert-butylsulfanyl)(aryl)diazenes, see: (a) van Zwet, H.; Kooyman, E. C. Recl. Trav. Chim. Pays-Bas 1967, 86, 993. (b) van Beek, L. K. H.; van Beek, G. C. Jr.; Boven, J.; Schoot, C. J. J. Org. Chem. 1971, 36, 2194. (c) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron 1973, 29, 4169. (d) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron Lett. 1974, 49. (e) Petrillo, G.; Novi, M.; Dell'Erba, C.; Tavani, C.; Berta, G. Tetrahedron 1990, 46, 7977; and references therein. (f) Caposcialli, N.; Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1998, 54, 3529; and references therein.
3. For some examples on the preparation, stability and synthetic applications of (Z)-(tert-butylsulfanyl)(aryl)diazenes, see: (a) van Zwet, H.; Kooyman, E. C. Recl. Trav. Chim. Pays-Bas 1967, 86, 993. (b) van Beek, L. K. H.; van Beek, G. C. Jr.; Boven, J.; Schoot, C. J. J. Org. Chem. 1971, 36, 2194. (c) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron 1973, 29, 4169. (d) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron Lett. 1974, 49. (e) Petrillo, G.; Novi, M.; Dell'Erba, C.; Tavani, C.; Berta, G. Tetrahedron 1990, 46, 7977; and references therein. (f) Caposcialli, N.; Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1998, 54, 3529; and references therein.
4. For some examples on the preparation, stability and synthetic applications of (Z)-(tert-butylsulfanyl)(aryl)diazenes, see: (a) van Zwet, H.; Kooyman, E. C. Recl. Trav. Chim. Pays-Bas 1967, 86, 993. (b) van Beek, L. K. H.; van Beek, G. C. Jr.; Boven, J.; Schoot, C. J. J. Org. Chem. 1971, 36, 2194. (c) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron 1973, 29, 4169. (d) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron Lett. 1974, 49. (e) Petrillo, G.; Novi, M.; Dell'Erba, C.; Tavani, C.; Berta, G. Tetrahedron 1990, 46, 7977; and references therein. (f) Caposcialli, N.; Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1998, 54, 3529; and references therein.
5. For some examples on the preparation, stability and synthetic applications of (Z)-(tert-butylsulfanyl)(aryl)diazenes, see: (a) van Zwet, H.; Kooyman, E. C. Recl. Trav. Chim. Pays-Bas 1967, 86, 993. (b) van Beek, L. K. H.; van Beek, G. C. Jr.; Boven, J.; Schoot, C. J. J. Org. Chem. 1971, 36, 2194. (c) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron 1973, 29, 4169. (d) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron Lett. 1974, 49. (e) Petrillo, G.; Novi, M.; Dell'Erba, C.; Tavani, C.; Berta, G. Tetrahedron 1990, 46, 7977; and references therein. (f) Caposcialli, N.; Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1998, 54, 3529; and references therein.
6. For some examples on the preparation, stability and synthetic applications of (Z)-(tert-butylsulfanyl)(aryl)diazenes, see: (a) van Zwet, H.; Kooyman, E. C. Recl. Trav. Chim. Pays-Bas 1967, 86, 993. (b) van Beek, L. K. H.; van Beek, G. C. Jr.; Boven, J.; Schoot, C. J. J. Org. Chem. 1971, 36, 2194. (c) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron 1973, 29, 4169. (d) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron Lett. 1974, 49. (e) Petrillo, G.; Novi, M.; Dell'Erba, C.; Tavani, C.; Berta, G. Tetrahedron 1990, 46, 7977; and references therein. (f) Caposcialli, N.; Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1998, 54, 3529; and references therein.
7. For some examples on the preparation, stability and synthetic applications of (Z)-(tert-butylsulfanyl)(aryl)diazenes, see: (a) van Zwet, H.; Kooyman, E. C. Recl. Trav. Chim. Pays-Bas 1967, 86, 993. (b) van Beek, L. K. H.; van Beek, G. C. Jr.; Boven, J.; Schoot, C. J. J. Org. Chem. 1971, 36, 2194. (c) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron 1973, 29, 4169. (d) Brokken-Zijp, J.; van de Bogaert, H. Tetrahedron Lett. 1974, 49. (e) Petrillo, G.; Novi, M.; Dell'Erba, C.; Tavani, C.; Berta, G. Tetrahedron 1990, 46, 7977; and references therein. (f) Caposcialli, N.; Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1998, 54, 3529; and references therein.
8. For examples, see: (a) Gross, M. L.; Blank, D. H.; Welch, W. M. J. Org. Chem. 1993, 58, 2104; and references therein. (b) Lazny, R.; Poplawski, J.; Kobberling, J.; Enders, D.; Brase, S. Synlett 1999, 1304; and references therein. (c) Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.; Fochi, R. Synthesis 2001, 2180; and references therein.
9. For examples, see: (a) Gross, M. L.; Blank, D. H.; Welch, W. M. J. Org. Chem. 1993, 58, 2104; and references therein. (b) Lazny, R.; Poplawski, J.; Kobberling, J.; Enders, D.; Brase, S. Synlett 1999, 1304; and references therein. (c) Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.; Fochi, R. Synthesis 2001, 2180; and references therein.
10. For examples, see: (a) Gross, M. L.; Blank, D. H.; Welch, W. M. J. Org. Chem. 1993, 58, 2104; and references therein. (b) Lazny, R.; Poplawski, J.; Kobberling, J.; Enders, D.; Brase, S. Synlett 1999, 1304; and references therein. (c) Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.; Fochi, R. Synthesis 2001, 2180; and references therein.
11. Recent reviews on N-monoalkylation of anilines: (a) Wurziger, H. Kontakte (Darmstadt) 1987, 3, 8; Chem. Abstr. 1988, 109: 109906. (b) Xiaojian, Z.; Zuwang, W. Huagong Jinzhan 1996, 5; Chem. Abstr. 1996, 124, 320046.
12. Recent reviews on N-monoalkylation of anilines: (a) Wurziger, H. Kontakte (Darmstadt) 1987, 3, 8; Chem. Abstr. 1988, 109: 109906. (b) Xiaojian, Z.; Zuwang, W. Huagong Jinzhan 1996, 5; Chem. Abstr. 1996, 124, 320046.
13. Recent reviews on N-monoalkylation of anilines: (a) Wurziger, H. Kontakte (Darmstadt) 1987, 3, 8; Chem. Abstr. 1988, 109: 109906. (b) Xiaojian, Z.; Zuwang, W. Huagong Jinzhan 1996, 5; Chem. Abstr. 1996, 124, 320046.
14. Recent reviews on N-monoalkylation of anilines: (a) Wurziger, H. Kontakte (Darmstadt) 1987, 3, 8; Chem. Abstr. 1988, 109: 109906. (b) Xiaojian, Z.; Zuwang, W. Huagong Jinzhan 1996, 5; Chem. Abstr. 1996, 124, 320046.
15. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
16. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
17. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
18. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
19. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
20. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
21. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
22. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
23. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
24. Some recent examples on the N-monoalkylation of anilines: (a) Wimmer, P.; Buysch, H. J.; Puppe, L.; Froehlich, C. Bayer A.-G., Eur. Pat. 410243, 1991; Chem. Abstr. 1991, 115, 8274f. (b) Pappas, P. G.; Melville, J. B. Amoco Corp. USA, US Pat. 5159115, 1992; Chem. Abstr. 1993, 118, 41193p. (c) Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121. (d) Ivanov, E. I.; Polishchuk, A. A. Zh. Obshch. Khim. 1993, 63, 403. (e) Matsuo, K.; Shichida, Y.; Nishida, H.; Nakata, S.; Okuba, M. J. Phys. Org. Chem. 1994, 7, 9. (f) Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777; and references therein. (g) Sreekumar, K.; Jyothi, T. M.; Talawar, M. B.; Kiran, B. P.; Rao, B. S.; Sugunan, S. J. Mol. Catal. A: Chem. 2000, 152, 225; and references therein. (h) Sreekumar, K.; Jyothi, T. M.; Govindankutty, R. C.; Rao, B. S.; Sugunan, S. React. Kinet. Catal. Lett. 2000, 70, 161; and references therein. (i) Zhang, R.; Wu, Z.; Lin, L.; Yang, H. SEPU 2000, 18, 532; Chem. Abstr. 2001, 134, 162664.
25. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
26. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
27. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
28. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
29. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
30. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
31. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
32. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
33. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
34. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
35. Some recent examples on the synthesis of N-monoalkylanilines, apart from N-monoalkylation of anilines: (a) Mićović, I. V.; Ivanović, M. D.; Piantak, D. M.; Bojić, V. Dj Synthesis 1991, 1043. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268. (e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066. (f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641; and references therein. (g) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459. (h) Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144; and references therein. (j) Periasamy, M. M.; Natarajan Jayakumart, K.; Bharathi, P. J. Org. Chem. 2000, 65, 3548. (k) Bae, J. W.; Cho, Y. J.; Lee, S. W.; Yoon, C.-O. M.; Yoon, C. M. Chem. Commun. 2000, 1857.
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