Synthesis of Spiro Polycyclic Aromatic Hydrocarbons by Intramolecular Palladium-Catalyzed Arylation

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1286-1291

  González, Juan J ^a   Garćia, Nuria ^a   Gómez Lor, Berta ^a   Echavarren, Antonio M ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041799132     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962059n     Document Type: Article

References (59)

1. Synthesis of heterocycles by palladium-catalyzed arylation: (a) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (b) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (c) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919. (d) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1991, 32, 6915. (e) Kozikowski, A. P.; Ma, D. Tetrahedron Lett. 1991, 32, 3317.
2. Synthesis of heterocycles by palladium-catalyzed arylation: (a) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (b) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (c) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919. (d) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1991, 32, 6915. (e) Kozikowski, A. P.; Ma, D. Tetrahedron Lett. 1991, 32, 3317.
3. Synthesis of heterocycles by palladium-catalyzed arylation: (a) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (b) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (c) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919. (d) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1991, 32, 6915. (e) Kozikowski, A. P.; Ma, D. Tetrahedron Lett. 1991, 32, 3317.
4. Synthesis of heterocycles by palladium-catalyzed arylation: (a) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (b) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (c) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919. (d) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1991, 32, 6915. (e) Kozikowski, A. P.; Ma, D. Tetrahedron Lett. 1991, 32, 3317.
5. Synthesis of heterocycles by palladium-catalyzed arylation: (a) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (b) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (c) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919. (d) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1991, 32, 6915. (e) Kozikowski, A. P.; Ma, D. Tetrahedron Lett. 1991, 32, 3317.
6. Application of the palladium-catalyzed arylation to the synthesis of biaryls: (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Stadibauer, W.; Laschober, R.; Kappe, T. Liebigs Ann. Chem. 1990, 531. (c) Deshpande, P. P.; Martin, O. R. Tetrahedron Lett. 1990, 31, 6313. (d) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. (e) Bringmann, G.; Keller, P. A.; Rölfing, K. Synlett 1994, 423.
7. Application of the palladium-catalyzed arylation to the synthesis of biaryls: (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Stadibauer, W.; Laschober, R.; Kappe, T. Liebigs Ann. Chem. 1990, 531. (c) Deshpande, P. P.; Martin, O. R. Tetrahedron Lett. 1990, 31, 6313. (d) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. (e) Bringmann, G.; Keller, P. A.; Rölfing, K. Synlett 1994, 423.
8. Application of the palladium-catalyzed arylation to the synthesis of biaryls: (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Stadibauer, W.; Laschober, R.; Kappe, T. Liebigs Ann. Chem. 1990, 531. (c) Deshpande, P. P.; Martin, O. R. Tetrahedron Lett. 1990, 31, 6313. (d) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. (e) Bringmann, G.; Keller, P. A.; Rölfing, K. Synlett 1994, 423.
9. Application of the palladium-catalyzed arylation to the synthesis of biaryls: (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Stadibauer, W.; Laschober, R.; Kappe, T. Liebigs Ann. Chem. 1990, 531. (c) Deshpande, P. P.; Martin, O. R. Tetrahedron Lett. 1990, 31, 6313. (d) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. (e) Bringmann, G.; Keller, P. A.; Rölfing, K. Synlett 1994, 423.
10. Application of the palladium-catalyzed arylation to the synthesis of biaryls: (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. (b) Stadibauer, W.; Laschober, R.; Kappe, T. Liebigs Ann. Chem. 1990, 531. (c) Deshpande, P. P.; Martin, O. R. Tetrahedron Lett. 1990, 31, 6313. (d) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. (e) Bringmann, G.; Keller, P. A.; Rölfing, K. Synlett 1994, 423.
11. Synthesis of carbocycles by palladium-catalyzed arylation: (a) Rice, J. E.; Cai, Z.-W.; He, Z.-M.; LaVoie, E. J. J. Org. Chem. 1995, 60, 8101. (b) Rice, J. E.; Cai, Z.-W. J. Org. Chem. 1993, 58, 1415. (c) Rice, J. E.; Cai, Z.-W. Tetrahedron Lett. 1992, 33, 1675.
12. Synthesis of carbocycles by palladium-catalyzed arylation: (a) Rice, J. E.; Cai, Z.-W.; He, Z.-M.; LaVoie, E. J. J. Org. Chem. 1995, 60, 8101. (b) Rice, J. E.; Cai, Z.-W. J. Org. Chem. 1993, 58, 1415. (c) Rice, J. E.; Cai, Z.-W. Tetrahedron Lett. 1992, 33, 1675.
13. Synthesis of carbocycles by palladium-catalyzed arylation: (a) Rice, J. E.; Cai, Z.-W.; He, Z.-M.; LaVoie, E. J. J. Org. Chem. 1995, 60, 8101. (b) Rice, J. E.; Cai, Z.-W. J. Org. Chem. 1993, 58, 1415. (c) Rice, J. E.; Cai, Z.-W. Tetrahedron Lett. 1992, 33, 1675.
14. For the intermolecular palladium-catalyzed arylation, see: (a) Akita, Y.; Inoue, A.; Yamamoto, K.; Ohta, A.; Kurihara, T.; Shimizu, M. Heterocycles 1985, 23, 2327. (b) Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Tokunaga, K.; Gohma, K.; Komatsu, J.; Sekine, K.; Miyafuji, A.; Kunoh, J.; Honma, R.; Akita, Y.; Ohta, A. Heterocycles 1992, 33, 257. (c) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023. (d) Dyker, G. J. Org. Chem. 1993, 58, 6426. (e) Dyker, G. Chem. Ber. 1994, 127, 739.
15. For the intermolecular palladium-catalyzed arylation, see: (a) Akita, Y.; Inoue, A.; Yamamoto, K.; Ohta, A.; Kurihara, T.; Shimizu, M. Heterocycles 1985, 23, 2327. (b) Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Tokunaga, K.; Gohma, K.; Komatsu, J.; Sekine, K.; Miyafuji, A.; Kunoh, J.; Honma, R.; Akita, Y.; Ohta, A. Heterocycles 1992, 33, 257. (c) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023. (d) Dyker, G. J. Org. Chem. 1993, 58, 6426. (e) Dyker, G. Chem. Ber. 1994, 127, 739.
16. For the intermolecular palladium-catalyzed arylation, see: (a) Akita, Y.; Inoue, A.; Yamamoto, K.; Ohta, A.; Kurihara, T.; Shimizu, M. Heterocycles 1985, 23, 2327. (b) Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Tokunaga, K.; Gohma, K.; Komatsu, J.; Sekine, K.; Miyafuji, A.; Kunoh, J.; Honma, R.; Akita, Y.; Ohta, A. Heterocycles 1992, 33, 257. (c) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023. (d) Dyker, G. J. Org. Chem. 1993, 58, 6426. (e) Dyker, G. Chem. Ber. 1994, 127, 739.
17. For the intermolecular palladium-catalyzed arylation, see: (a) Akita, Y.; Inoue, A.; Yamamoto, K.; Ohta, A.; Kurihara, T.; Shimizu, M. Heterocycles 1985, 23, 2327. (b) Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Tokunaga, K.; Gohma, K.; Komatsu, J.; Sekine, K.; Miyafuji, A.; Kunoh, J.; Honma, R.; Akita, Y.; Ohta, A. Heterocycles 1992, 33, 257. (c) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023. (d) Dyker, G. J. Org. Chem. 1993, 58, 6426. (e) Dyker, G. Chem. Ber. 1994, 127, 739.
18. For the intermolecular palladium-catalyzed arylation, see: (a) Akita, Y.; Inoue, A.; Yamamoto, K.; Ohta, A.; Kurihara, T.; Shimizu, M. Heterocycles 1985, 23, 2327. (b) Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Tokunaga, K.; Gohma, K.; Komatsu, J.; Sekine, K.; Miyafuji, A.; Kunoh, J.; Honma, R.; Akita, Y.; Ohta, A. Heterocycles 1992, 33, 257. (c) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023. (d) Dyker, G. J. Org. Chem. 1993, 58, 6426. (e) Dyker, G. Chem. Ber. 1994, 127, 739.
19. Pd(0) may coordinate with the added halide to form reactive anionic species: (a) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 1670. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (c) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605. (e) Amatore, C.; Carre, E.; Jutand, A.; Tanaka, H.; Ren, Q.; Torii, S. Chem. Eur. J. 1996, 2, 957.
20. Pd(0) may coordinate with the added halide to form reactive anionic species: (a) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 1670. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (c) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605. (e) Amatore, C.; Carre, E.; Jutand, A.; Tanaka, H.; Ren, Q.; Torii, S. Chem. Eur. J. 1996, 2, 957.
21. Pd(0) may coordinate with the added halide to form reactive anionic species: (a) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 1670. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (c) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605. (e) Amatore, C.; Carre, E.; Jutand, A.; Tanaka, H.; Ren, Q.; Torii, S. Chem. Eur. J. 1996, 2, 957.
22. Pd(0) may coordinate with the added halide to form reactive anionic species: (a) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 1670. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (c) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605. (e) Amatore, C.; Carre, E.; Jutand, A.; Tanaka, H.; Ren, Q.; Torii, S. Chem. Eur. J. 1996, 2, 957.
23. Pd(0) may coordinate with the added halide to form reactive anionic species: (a) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 1670. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (c) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605. (e) Amatore, C.; Carre, E.; Jutand, A.; Tanaka, H.; Ren, Q.; Torii, S. Chem. Eur. J. 1996, 2, 957.
24. Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 3.4, pp 228-229.
25. (a) An electrophilic pathway has been shown to operate in somewhat related palladation reactions: Canty, A. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 9, Chapter 5 and references cited therein.
26. (b) The synthesis of palladacycles by intramolecular palladation of an aryl ring has been demonstrated to proceed by electrophilic substitution: Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1992, 425, 151.
27. 3b
28. Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235.
29. 3NBr (2-3 equiv).
30. 2 as the catalyst gave 10 in 30% yield. The use of DBU, 1,8-bis(dimethylamino)naphthalene, and N-methylimidazole as the base and/or ligand for Pd gave only recovered starting material.
31. Benz[e]acephenanthrylenes are an important class of environmental carcinogens. For recent syntheses, see: (a) Cho, B. P.; Zhou, L. Tetrahedron Lett. 1996, 37, 1535. (b) Cho, B. P. Tetrahedron Lett. 1995, 36, 2403. (c) Tanga, M. J.; Bupp, J. E. J. Org. Chem. 1993, 58, 4173. (d) Cho, B. P.; Kim, M.; Harvey, R. G. J. Org. Chem. 1993, 58, 5788. (e) Cho, B. P.; Harvey, R. G. J. Org. Chem. 1987, 52, 5668. (f) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Carmella, S. G.; Hecht, S. J. Org. Chem. 1986, 51, 1206. (g) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Hecht, S. S. J. Org. Chem. 1985, 50, 1948.
32. Benz[e]acephenanthrylenes are an important class of environmental carcinogens. For recent syntheses, see: (a) Cho, B. P.; Zhou, L. Tetrahedron Lett. 1996, 37, 1535. (b) Cho, B. P. Tetrahedron Lett. 1995, 36, 2403. (c) Tanga, M. J.; Bupp, J. E. J. Org. Chem. 1993, 58, 4173. (d) Cho, B. P.; Kim, M.; Harvey, R. G. J. Org. Chem. 1993, 58, 5788. (e) Cho, B. P.; Harvey, R. G. J. Org. Chem. 1987, 52, 5668. (f) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Carmella, S. G.; Hecht, S. J. Org. Chem. 1986, 51, 1206. (g) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Hecht, S. S. J. Org. Chem. 1985, 50, 1948.
33. Benz[e]acephenanthrylenes are an important class of environmental carcinogens. For recent syntheses, see: (a) Cho, B. P.; Zhou, L. Tetrahedron Lett. 1996, 37, 1535. (b) Cho, B. P. Tetrahedron Lett. 1995, 36, 2403. (c) Tanga, M. J.; Bupp, J. E. J. Org. Chem. 1993, 58, 4173. (d) Cho, B. P.; Kim, M.; Harvey, R. G. J. Org. Chem. 1993, 58, 5788. (e) Cho, B. P.; Harvey, R. G. J. Org. Chem. 1987, 52, 5668. (f) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Carmella, S. G.; Hecht, S. J. Org. Chem. 1986, 51, 1206. (g) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Hecht, S. S. J. Org. Chem. 1985, 50, 1948.
34. Benz[e]acephenanthrylenes are an important class of environmental carcinogens. For recent syntheses, see: (a) Cho, B. P.; Zhou, L. Tetrahedron Lett. 1996, 37, 1535. (b) Cho, B. P. Tetrahedron Lett. 1995, 36, 2403. (c) Tanga, M. J.; Bupp, J. E. J. Org. Chem. 1993, 58, 4173. (d) Cho, B. P.; Kim, M.; Harvey, R. G. J. Org. Chem. 1993, 58, 5788. (e) Cho, B. P.; Harvey, R. G. J. Org. Chem. 1987, 52, 5668. (f) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Carmella, S. G.; Hecht, S. J. Org. Chem. 1986, 51, 1206. (g) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Hecht, S. S. J. Org. Chem. 1985, 50, 1948.
35. Benz[e]acephenanthrylenes are an important class of environmental carcinogens. For recent syntheses, see: (a) Cho, B. P.; Zhou, L. Tetrahedron Lett. 1996, 37, 1535. (b) Cho, B. P. Tetrahedron Lett. 1995, 36, 2403. (c) Tanga, M. J.; Bupp, J. E. J. Org. Chem. 1993, 58, 4173. (d) Cho, B. P.; Kim, M.; Harvey, R. G. J. Org. Chem. 1993, 58, 5788. (e) Cho, B. P.; Harvey, R. G. J. Org. Chem. 1987, 52, 5668. (f) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Carmella, S. G.; Hecht, S. J. Org. Chem. 1986, 51, 1206. (g) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Hecht, S. S. J. Org. Chem. 1985, 50, 1948.
36. Benz[e]acephenanthrylenes are an important class of environmental carcinogens. For recent syntheses, see: (a) Cho, B. P.; Zhou, L. Tetrahedron Lett. 1996, 37, 1535. (b) Cho, B. P. Tetrahedron Lett. 1995, 36, 2403. (c) Tanga, M. J.; Bupp, J. E. J. Org. Chem. 1993, 58, 4173. (d) Cho, B. P.; Kim, M.; Harvey, R. G. J. Org. Chem. 1993, 58, 5788. (e) Cho, B. P.; Harvey, R. G. J. Org. Chem. 1987, 52, 5668. (f) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Carmella, S. G.; Hecht, S. J. Org. Chem. 1986, 51, 1206. (g) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Hecht, S. S. J. Org. Chem. 1985, 50, 1948.
37. Benz[e]acephenanthrylenes are an important class of environmental carcinogens. For recent syntheses, see: (a) Cho, B. P.; Zhou, L. Tetrahedron Lett. 1996, 37, 1535. (b) Cho, B. P. Tetrahedron Lett. 1995, 36, 2403. (c) Tanga, M. J.; Bupp, J. E. J. Org. Chem. 1993, 58, 4173. (d) Cho, B. P.; Kim, M.; Harvey, R. G. J. Org. Chem. 1993, 58, 5788. (e) Cho, B. P.; Harvey, R. G. J. Org. Chem. 1987, 52, 5668. (f) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Carmella, S. G.; Hecht, S. J. Org. Chem. 1986, 51, 1206. (g) Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Hecht, S. S. J. Org. Chem. 1985, 50, 1948.
38. For the formation of reduced products under palladium-catalyzed conditions, see: Saá, J. M.; Dopico, M.; Martorell, G.; García-Raso, A. J. Org. Chem. 1990, 55, 991 and references cited therein.
39. Stille, J. K. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: Chichester, 1985; Vol. 2, Chapter 9.
40. Klemm, L. M.; Huber, E.; Klopfenstein, C. E. J. Org. Chem. 1964, 29, 1960.
41. 1b
42. Gretz, E.; Sen, A. J. Am. Chem. Soc. 1986, 108, 6038.
43. 2 fashion: (a) Li, C.-S.; Jou, D.-C.; Cheng, C.-H. Organometallics 1993, 12, 3945. (b) Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710. (c) Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169.
44. 2 fashion: (a) Li, C.-S.; Jou, D.-C.; Cheng, C.-H. Organometallics 1993, 12, 3945. (b) Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710. (c) Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169.
45. 2 fashion: (a) Li, C.-S.; Jou, D.-C.; Cheng, C.-H. Organometallics 1993, 12, 3945. (b) Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710. (c) Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169.
46. 3 with (diphosphine)platinum dichloride complexes led to (diphosphine)platinum carbonate complexes: (a) Andrews, M. A.; Gould, G. L.; Voss, E. J. Inorg. Chem. 1996, 35, 5740. (b) Andrews, M. A.; Gould, G. L.; Klooster, W. T.; Koening, K. S.; Voss, E. J. Inorg. Chem. 1996, 35, 5478 and references cited therein. (c) For the formation of bis(triphenylphosphino)carbonatopalladium: Nyman, C. J.; Wymore, C. E.; Wilkinson, G. J. Chem. Soc. A 1968, 561.
47. 3 with (diphosphine)platinum dichloride complexes led to (diphosphine)platinum carbonate complexes: (a) Andrews, M. A.; Gould, G. L.; Voss, E. J. Inorg. Chem. 1996, 35, 5740. (b) Andrews, M. A.; Gould, G. L.; Klooster, W. T.; Koening, K. S.; Voss, E. J. Inorg. Chem. 1996, 35, 5478 and references cited therein. (c) For the formation of bis(triphenylphosphino)carbonatopalladium: Nyman, C. J.; Wymore, C. E.; Wilkinson, G. J. Chem. Soc. A 1968, 561.
48. 3 with (diphosphine)platinum dichloride complexes led to (diphosphine)platinum carbonate complexes: (a) Andrews, M. A.; Gould, G. L.; Voss, E. J. Inorg. Chem. 1996, 35, 5740. (b) Andrews, M. A.; Gould, G. L.; Klooster, W. T.; Koening, K. S.; Voss, E. J. Inorg. Chem. 1996, 35, 5478 and references cited therein. (c) For the formation of bis(triphenylphosphino)carbonatopalladium: Nyman, C. J.; Wymore, C. E.; Wilkinson, G. J. Chem. Soc. A 1968, 561.
49. Rice, J. E.; Czech, A.; Hussain, N.; LaVoie, E. J. J. Org. Chem. 1988, 53, 1775.
50. (a) Lee-Ruff, E.; Kruk, H.; Katz, M. J. Org. Chem. 1984, 49, 553.
51. (b) Harvey, R. G.; Abu-shqara, E.; Yang, C. J. Org. Chem. 1992, 57, 6313.
52. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
53. Breslow, R.; Garratt, S.; Kaplan, L.; LaPollette, D. J. Am. Chem. Soc. 1968, 90, 4051.
54. Lisitsyn, V. N.; Lugovskaya, E. K. Zh. Org. Khim. 1974, 10, 92.
55. Carson, J. R.; Almond, H. R.; Brannan, M. D.; Carmosin, R. J.; Flaim, S. F.; Gill, A.; Gleason, M. M.; Keely, S. L.; Ludovici, D. W.; Pitis, P. M.; Rebarchak, M. C.; Villani, F. J. J. Med. Chem. 1988, 31, 630.
56. Alternatively, palladium-catalyzed reaction of 9-(2-bromobenzylidene)fluorene afforded 10 in 44% yield.
57. 12f gave 11 in 32% yield.
58. 13C NMR spectra are provided as Supporting Information.
59. 21b