

|
|
|
|
III.2.5 |
PALLADIUM-CATALYZED ARYL–ARYL COUPLING |
331 |
||||||
TABLE 11. (Continued ) |
|
|
|
|
|
|
|
|||||
|
|
|
|
ArMX Ar Y |
Cat. |
Ar – Ar |
|
|
|
|||
|
|
|
|
9: |
|
|
|
|||||
|
|
|
|
|
|
|
|
|
|
|
||
Entry |
|
|
|
Substrates |
|
|
MX |
Catalyst |
Yield (%) |
Reference |
||
|
|
|
|
|
|
|
|
|
|
|
|
|
4 |
|
|
|
|
|
|
|
MgBr |
Pd(acac)2 |
50 |
[126] |
|
|
|
|
|
|
|
|
|
|||||
|
|
|
|
|
|
|||||||
|
|
MX |
Br |
|
|
|
MgBr |
NiBr2, dppf |
77 |
[127] |
|
|
|
|
|
|
|
|
|||||||
O |
|
|
OCH2Ph |
PhH2CO |
|
|
|
|
|
|
|
|
|
|
MX |
Br |
|
|
B(OH)2 |
Pd(PPh3)4, Na2CO3 |
|
|
|
||
5 |
|
|
|
|
12 |
[128] |
|
|||||
OtBu |
|
|
OCH2Ph |
|
|
|
|
|
|
|
|
|
|
|
PhH2CO |
|
|
|
|
|
|
|
|||
|
|
|
|
|
|
|
|
|
|
|||
Bn |
|
|
|
|
|
|
|
|
|
|
|
|
|
N |
|
|
|
|
|
|
|
|
|
||
|
|
|
|
|
|
|
OMe |
|
|
|
|
|
BnO |
|
|
MX |
TfO |
|
OAc |
|
|
|
|
||
|
|
|
|
|
|
|
||||||
6 |
|
|
OBn |
|
|
|
|
B(OH)2 |
Pd(PPh3)4, Ba(OH)2 |
74 |
[129] |
|
|
|
|
|
|
|
|
||||||
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
AcO |
|
OTf |
|
|
|
|
MeO
aAryl electrophiles are arranged according to increasing order of priority determined by the Cahn–Ingold–Prelog rule.
REFERENCES
[1]R. C. Larock, in Comprehensive Organic Transformations: A Guide to Functional Group Preparations, Wiley-VCH New York, 1999, Chap. 2, 77–128.
[2]G. H. Posner, Org. React., 1975, 22, 253– 400.
[3]M. F. Semmelhack, P. M. Helquist, and L. D. Jones, J. Am. Chem. Soc., 1971, 93, 5908.
[4]K. Tamao, K. Sumitani, and M. Kumada, J. Am. Chem. Soc., 1972, 94, 4374.
[5]R. J. P. Corriu and J. P. Masse, J. Chem. Soc. Chem. Commun., 1972, 144.
[6]M. Kumada, Pure Appl. Chem., 1980, 52, 669–679.
[7]K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada, Bull. Chem. Soc. Jpn., 1976, 49, 1958.
[8]A. Sekiya and N. Ishikawa, J. Organomet. Chem., 1976, 118, 349.
[9]E. Negishi, A. O. King, and N. Okukado, J. Org. Chem., 1977, 42, 1821.
[10]E. R. Larson and R. A. Raphael, Tetrahedron Lett., 1979, 5041.
[11]E. Negishi, T. Takahashi, and A. O. King, Org. Synth; 1985, 66, 67.
[12]N. Miyaura, T. Yanagi, and A. Suzuki, Synth. Commun., 1981, 11, 513.
[13]N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457–2483.
[14]A. N. Kashin, I. G. Bumagina, N. A. Bumagin, and I. P. Beletskaya, Zh. Org. Khim., 1981, 17, 21.
[15]J. K. Stille, Angew. Chem. Int. Ed. Engl., 1986, 25, 508–524.
[16]V. Farina, V. Krishnamurthy, and W. J. Scott, Org. React., 1997, 50, 1–652.
[17]T. R. Hoye and M. Chen, J. Org. Chem., 1996, 61, 7940
332III Pd-CATALYZED CROSS-COUPLING
[18]M. R. Agharahimi and N. A. LeBel, J. Org. Chem., 1995, 60, 1856.
[19]S. P. Stanforth, Tetrahedron, 1998, 54, 263–303 (and references cited therein).
[20]G. P. Roth and C. E. Fuller, J. Org. Chem., 1991, 56, 3493.
[21]C. A. Quesnelle, O. B. Familoni, and V. Snieckus, Syn lett, 1994, 349.
[22]T. Oh-e, N. Miyaura, and A. Suzuki, J. Org. Chem., 1993, 58, 2201.
[23]V. Aranyos, A. M. Castnao, and H. Grennberg, Acta Chem. Scand., 1999, 53, 714.
[24]K. Koch, R. J. Chambers, and M. S. Biggers, Synlett, 1994, 347.
[25]S. Saito, S. Oh-tani, and N. Miyaura, J. Org. Chem., 1997, 62, 8024.
[26]J. A. Miller and R. P. Farrell, Tetrahedron Lett., 1998, 39, 6441.
[27]J. Huang and S. P. Nolan, J. Am. Chem. Soc., 1999, 121, 9889.
[28]X. Bei, H. W. Turner, W. H. Weinberg, and Anil S. Guram, J. Org. Chem., 1999, 64, 6797.
[29]J. Galland, M. Savignac, and J. Genet, Tetrahedron Lett., 1999, 40, 2323.
[30]D. Milstein and J. K. Stille, J. Am. Chem. Soc., 1979, 101, 4992.
[31]H. Ito, H. Sensui, K. Arimoto, K. Miura, and A. Hosomi, Chem. Lett., 1997, 639.
[32]Y. Okamoto, K. Yoshioka, T. Yamana, and H. Mori, J. Organomet. Chem., 1989, 369, 285.
[33]G. Marck, A. Villiger, and R. Buchecker, Tetrahedron Lett., 1994, 35, 3277.
[34]M. Hoshino, P. Degenkolb, and D. P. Curran, J. Org. Chem., 1997, 62, 8341.
[35]M. Sato, N. Miyaura, and A. Suzuki, Chem. Lett., 1989, 1405.
[36]N. A. Bumagin, A. B. Ponomaryov, and I. P. Beletskaya, J. Organomet. Chem., 1985, 291, 129.
[37]M. Catellani, G. Chiusoli, and V. Fornasari, Gazz. Chim. Ital., 1990, 120, 779.
[38]M. Kosugi, T. Ishikawa, T. Nogami, and T. Migita, Nippon Kagaku Kaishi, 1985, 520.
[39]D. P. G. Hamon, R. A. Massy-Westropp, and J. L. Newton, Tetrahedron, 1995, 51, 12645.
[40]S. Chamoin, S. Houldsworth, C. G. Kruse, W. I. Bakker, and V. Snieckus, Tetrahedron Lett., 1998, 39, 4179.
[41]N. A. Bumagin, V. V. Bykov, and I. P. Beletskaya, Izv. Akad. Nauk. SSSR Ser. Khim., 1989, 38, 2394.
[42]S. K. Kang, J. S. Kim, S. K. Yoon, K. H. Lin, and S. S. Yoon, Tetrahedron Lett., 1998, 39, 3011.
[43]N. A. Bumagin and E. V. Luzikova, J. Organomet. Chem., 1997, 532, 271.
[44]N. E. Leadbeater and S. M. Resouly, Tetrahedron, 1999, 55, 11889.
[45]V. V. Bykov and N. A. Bumagin, Russ. Chem. Bull., 1997, 46, 1344.
[46]R. Frenette and R. W. Friesen, Tetrahedron Lett., 1994, 35, 9177.
[47]S. Chamoin, S. Houldsworth, and V. Snieckus, Tetrahedron Lett., 1998, 39, 4175.
[48]J. P. Genêt, E. Blart, and M. Savignac, Synlett, 1992, 715.
[49]N. S. Kozlov, R. D. Sauts, and V. M. Prishchipenko, Dokl. Akad. Nauk SSSR, 1990, 311, 1133.
[50]L. A. Paquette, J. C. Lanter, and J. N. Johnston, J. Org. Chem., 1997, 62, 1702.
[51]E. Negishi, T. Takahashi, and K. Akiyoshi, J. Organomet. Chem., 1987, 334, 181.
[52]K. Yoon and D. Y. Son, Org. Lett., 1999, 1, 423.
[53]J. Clayden, J. J. A. Cooney, and M. Julia, J. Chem. Soc. Perkin Trans. 1, 1995, 7.
[54]J. Clayden and M. Julia, J. Chem. Soc. Chem. Commun., 1993, 1682.
[55]Y. Uozumi, H. Danjo, and T. Hayashi, J. Org. Chem., 1999, 64, 3384.
[56]Y. Hatanaka, K. Goda, Y. Okahara, and T. Hiyama, Tetrahedron, 1994, 50, 8301.
[57]R. S. Varma and K. P. Naicker, Tetrahedron Lett., 1999, 40, 439.
III.2.5 PALLADIUM-CATALYZED ARYL–ARYL COUPLING |
333 |
[58]D. Kaufmann, Chem. Ber., 1987, 120, 901.
[59]K. Hirabayashi, T. Kondo, F. Toriyama, Y. Nishihara, and A. Mori, Bull. Chem. Soc. Jpn., 2000, 73, 749.
[60]S. E. Denmark and Z. Wu, Org. Lett., 1999, 1, 1495.
[61]S. K. Kang, T. T. Baik, and S. Y. Song, Synlett, 1999, 327.
[62]U.S. Patent 5859247, January 12, 1999 (CAS 130:110408).
[63]S. K. Kang, H. W. Lee, S. B. Jang, and P. S. Ho, J. Org. Chem., 1996, 61, 4720.
[64]N. A. Bumagin and V. V. Bykov, Zh. Org. Khim., 1990, 66, 1981.
[65]I. Klement, M. Rottländer, C. E. Tucker, T. N. Majid, P. Knochel, P. Venegas, and G. Cahiez, Tetrahedron, 1996, 52, 7201.
[66]S. R. Piettre and S. Baltzer, Tetrahedron Lett., 1997, 38, 1197.
[67]D. W. Old, J. P. Wolfe, and S. L. Buchwald, J. Am. Chem. Soc., 1998, 120, 9722.
[68]W. Müeller, P. Kipfer, D. A. Lowe, and S. Urwyler, Helv. Chim. Acta, 1995, 78, 2026.
[69]W. Mueller, D. A. Lowe, H. Neijt, S. Urwyler, P. L. Herrling, D. Blaser, and D. Seebach,
Helv. Chim. Acta, 1992, 75, 855.
[70]T. R. Kelly, G. J. Bridger, and C. Zhao, J. Am. Chem. Soc., 1990, 112, 8024.
[71]Y. Yang, A. R. Martin, D. L. Nelson, and J. Regan, Heterocycles, 1992, 34, 1169.
[72]M. Hird, A. J. Seed, and K. J. Toyne, Synlett, 1999, 438.
[73]D. De and D. J. Krogstad, Org. Lett., 2000, 2, 879.
[74]E. Wenkert, E. L. Michelotti, C. S. Swindell, and M. Tingoli, J. Org. Chem., 1984, 49, 4894.
[75]D. Badone, M. Baroni, R. Cardamone, A. Ielmini, and U. Guzzi, J. Org. Chem., 1997, 62, 7170.
[76]S. W. Wright, D. L. Hageman, and L. D. McClure, J. Org. Chem., 1994, 59, 6095.
[77]M. Park, J. R. Buck, and C. J. Rizzo, Tetrahedron, 1998, 54, 12707.
[78]N. A. Bumagin, A. Nikolai, and V. V. Bykov, Tetrahedron, 1997, 53, 14437.
[79]Japanese Patent 06107646, April 19, 1999 (CAS 121:134105).
[80]N. A. Bumagin, A. F. Nikitina, and I. P. Beletskaya, Zh. Org. Khim., 1996, 32, 1861.
[81]K. Takagi, Chem. Lett., 1993, 469.
[82]G. S. Reddy and W. Tam, Organometallics, 1984, 3, 630.
[83]T. Katayama and M. Umeno, Chem. Lett., 1991, 2073.
[84]A. Minato, K. Tamao, T. Hayashi, K. Suzuki, and M. Kumada, Tetrahedron Lett., 1980, 21, 845.
[85]R. B. Miller and S. Dugar, Organometallics, 1984, 3, 1261.
[86]C. W. Holzapfel and C. Dwyer, Heterocycles, 1998, 48, 1513.
[87]A. F. Littke, C. Dai, and G. C. Fu, J. Am. Chem. Soc., 2000, 122, 4020.
[88]WO Patent O9640684, December 19, 1996 (CAS 126:131464).
[89]A. Palmgren, A. Thorarensen, and J. Bëckvall, J. Org. Chem., 1998, 63, 3764.
[90]Y. Sugihara, H. Takeda, and J. Nakayama, Eur. J. Org. Chem., 1999, 597.
[91]J. A. Miller and R. P. Farrell, Tetrahedron Lett., 1998, 39, 7275.
[92]J. P. Wolfe, R. A. Singer, B. H. Yang, and S. L. Buchwald, J. Am. Chem. Soc., 1999, 121, 9550.
[93]M. Ueda, A. Saitoh, S. Oh-tani, and N. Miyaura, Tetrahedron, 1998, 54, 13079.
[94]C. von dem Bussche-Hünnefeld, D. Bühring, C. B. Knobler, and D. J. Cram, Chem. Commun., 1995, 1085.
334III Pd-CATALYZED CROSS-COUPLING
[95]J. C. Anderson and H. Namli, Synlett, 1995, 765.
[96]T. Vinod and H. Harti, J. Org. Chem., 1990, 55, 881.
[97]T. R. Kelly, J. P. Sestelo, and I. Tellitu, J. Org. Chem., 1998, 63, 3655.
[98]K. Manabe, K. Okamura, T. Date, and K. Koga, J. Org. Chem., 1993, 58, 6692.
[99]T. Kamikawa and T. Hayashi, Synlett, 1997, 163.
[100]J. C. Adrian, Jr. and C. S. Wilcox, J. Am. Chem. Soc., 1989, 111, 8055.
[101]S. Jinno, T. Okita, and K. Inouye, Bioorg. Med. Chem. Lett., 1999, 9, 1029.
[102]T. Choshi, T. Sada, H. Fujimoto, C. Nagayama, E. Sugino, and S. Hibino, Tetrahedron Lett., 1996, 37, 2593.
[103]D. Li, B. Zhao, and E. J. LaVoie, J. Org. Chem., 2000, 65, 2802.
[104]Y. Ikoma, K. Ando, Y. Naoi, T. Akiyama, and A. Sugimori, Synth. Commun., 1991, 21, 481.
[105]C. Pascal, J. Dubois, D. Gúenard, L. Tchertanov, S. Thoret, and F. Guéritte, Tetrahedron, 1998, 54, 14737.
[106]M. Iwao, H. Takehara, S. Furukawa, and M. Watanabe, Heterocycles, 1993, 36, 1483.
[107]M. Iwao, H. Tekehara, S. Obata, and M. Watanabe, Heterocycles, 1994, 38, 1717.
[108]D. A. Widdowson and Y. Zhang, Tetrahedron, 1986, 42, 2111.
[109]T. R. Kelly, A. García, F. Lang, J. J. Walsh, K. V. Bhaskar, M. R. Boyd, R. Götz, P. A. Keller, R. Walter, and G. Bringmann, Tetrahedron Lett., 1994, 35, 7621.
[110]T. R. Hoye, M. Chen, L. Mi, and O. P. Priest, Tetrahedron Lett., 1994, 35, 8747.
[111]K. C. Nicolaou, M. Takayanagi, N. F. Jain, S. Natarajan, A. E. Koumbis, T. Bando, and
J.M. Ramanjulu, Angew. Chem. Int. Ed. Engl., 1998, 37, 2717.
[112]M. Uemura, H. Nishimura, K. Kamikawa, K. Nakayama, and Y. Hayashi, Tetrahedron Lett., 1994, 35, 1909.
[113]K. Kamikawa, T. Watanabe, and M. Uemura, Synlett, 1995, 1040.
[114]T. Watanabe, N. Miyaura, and A. Suzuki, Synlett, 1992, 207.
[115]J. M. Saá, G. Martorell, and A. Garcia-Raso, J. Org. Chem., 1992, 57, 678.
[116]J. M. Saá and G. Martorell, J. Org. Chem., 1993, 58, 1963.
[117]G. Bringmann, R. Gotz, P. A. Keller, R. Walter, P. Henschel, M. Schaffer, M. Stablein, T. R. Kelly, and M. R. Boyd, Heterocycles, 1994, 39, 503.
[118]G. Bringmann, R. Götz, S. Harmsen, J. Holenz, and R. Walter, Liebigs Ann. Chem., 1996, 2045.
[119]M. Uemura, A. Daimon, and Y. Hayashi, Chem. Commun., 1995, 1943.
[120]T. Hayashi, K. Hayashizaki, and Y. Ito, Tetrahedron Lett., 1989, 30, 215.
[121]T. Watanabe and M. Uemura, Chem. Commun., 1998, 871.
[122]K. Kamikawa, T. Watanabe, and M. Uemura, J. Org. Chem., 1996, 61, 1375.
[123]S. Miyano, S. Okada, T. Suzuki, S. Handa, and H. Hashimoto, Bull. Chem. Soc. Jpn., 1986, 59, 2044.
[124]S. Coleman and E. B. Grant, Tetrahedron Lett., 1993, 34, 2225.
[125]H. Brunner, G. Olschewski, and B. Nuber, Synthesis, 1999, 429.
[126]T. Frejd and T. Klingstedt, Acta Chem. Scand., 1989, 43, 670.
[127]M. G. Johnson and R. J. Foglesong, Tetrahedron Lett., 1997, 38, 7001.
[128]S. L. Colletti and R. L. Halterman, Tetrahedron Lett., 1989, 30, 3513.
[129]G. Bringmann, R. Götz, P. A. Keller, R. Walter, M. R. Boyd, F. Lang, A. Garcia, J. J. Walsh,
I.Tellita, K. V. Bhaskan, and T. R. Kelly, J. Org. Chem., 1998, 63, 1090.