Palladium-Catalyzed Coupling of Organolead Compounds with Olefins

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5748-5749

  Kang, Suk Ku ^a   Choi, Sang Chul ^a   Ryu, Hyung Chul ^a   Yamaguchi, Tokutaro ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001148530     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980577n     Document Type: Article

References (39)

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2. (b) de Meijere, A.; Meyer, F. E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
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13. 3 at room temperature for 10 min See: Kang, S.-K.; Shivkumar, U.; Ahn, C.; Choi, S.-C.; Kim, J.-S. Synth. Commun. 1997, 27, 1893-1897.
14. Morgan, J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1990, 715-720.
15. In the case of allylic alcohols, palladium-catalyzed reaction of organic halides usually affords β-substituted ketones or aldehydes rather than the β-substituted allylic alcohols. See: (a) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265-272. (b) Tamara, Y.; Yamada, Y.; Yoshida, Y.; Yoshida, Z.-i. Tetrahedron 1979, 35, 329-340 and references therein.
16. In the case of allylic alcohols, palladium-catalyzed reaction of organic halides usually affords β-substituted ketones or aldehydes rather than the β-substituted allylic alcohols. See: (a) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265-272. (b) Tamara, Y.; Yamada, Y.; Yoshida, Y.; Yoshida, Z.-i. Tetrahedron 1979, 35, 329-340 and references therein.
17. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
18. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
19. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
20. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
21. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
22. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
23. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
24. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
25. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
26. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
27. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
28. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
29. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
30. Recently, palladium-catalyzed arylation and alkenylation of 2,3-dihydrofuran has attracted considerable interest since it offers the possibility of carrying out asymmetric coupling reactions. Depending on the reaction conditions, the thermodynamically more stable 2-substituted 2,3-dihydrofurans or the less stable 2-substituted 2,5-dihydrofurans can be formed. 2,5-Dihydrofuran formation: (a) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Kang, S.-K.; Yamaguchi, T.; Kim, J.-S.; Choi, S.-C.; Ahn, C. Synth. Commun. 1997, 27, 1105-1110. Asymmetric version: (e) Louseleur, O.; Meire, P.; Pfaltz, A. Angew. Chem Int. Ed. Engl. 1996, 35, 200-203. (f) Kurihara, Y.; Sedeoka, M.; Shibasaki, M. Chem. Pharm. Bull. 1994, 42, 2357-2359. (g) Hillers, S.; Reiser, O. Synlett. 1997, 27, 1105-1110. 2,3-Dihydrofuran formation: (h) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (i) Millers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. Asymmetric version: (j) Ozawa F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1419-1421. (k) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277. (l) Ozawa F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505-2508. (m) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (n) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
31. (p-Methoxyphenyl)lead triacetate 1b was easily prepared from anisole by treatment of lead(IV) tetraacetate. See: Kozyrod, R. P.; Pinhey, J. T. Org. Synth. 1984, 62, 24-29.
32. 2 240.1311, found 240.1150.
33. Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetrahedron Lett. 1993, 34, 91-94.
34. Palladium-catalyzed phenylation of allylic cyclic carbonates with diphenyliodonium tetrafluoroborate without no occurrence of ring opening was recently reported: Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Jang, S.-B. Tetrahedron Lett. 1995, 36, 8047-8050.
35. Willemsens, L. C.; Spierenburg, D. de V. J.; Wolters, J. J. Organomet. Chem. 1972, 39, C61-C62.
36. Bell, H. C.; Kalman, J. R.; Pinhey, J. T.; Sternhell, S. Aust. J. Chem. 1979, 32, 1521-1530.
37. It was reported that the modification of ligands influences the efficiency in metal-metal exchange: Parkinson, C. J.; Pinhey, J. T.; Stoermer, M. J. J. Chem. Soc., Perkin Trans. 1 1992, 1911-1915.
38. 2 cannot be ruled out.
39. The oxidative addition of organostannanes to a palladium(0) complex has been known: Shirakawa, E.; Yoshida, H.; Hiyama, T. Tetrahedron Lett. 1997, 38, 5177-5180.