Investigations into ambient temperature biaryl coupling reactions

Tetrahedron

Volumn 53, Issue 44, 1997, Pages 15123-15134

  Anderson, James C ^a   Namli, Hilmi ^a   Roberts, Craig A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; ENVIRONMENTAL TEMPERATURE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0030826090     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10010-2     Document Type: Article

References (57)

1. For a review see Bringmann, G.: Walter, R.: Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991.
2. For some representative examples see (a) Noyori, R.; Takaya, H. Chem. Scr. 1985, 25, 83.
3. (b) Takaya, H.; Mashima, K.; Koyana, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629-635.
4. (c) Hayashi, T. Acta Chemica Scandinavica 1996, 50, 259-266.
5. (d) Singer, R.A.; Carreira, E.M. J. Am Chem. Soc. 1995, 117, 12360-12361.
6. (e) Smrcina, M.; Poláková, J.; Vyskocil, S.; Kocovsky, P. J. Org. Chem. 1993, 58, 4534-4538.
7. (a) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732-8733.
8. (b) Moorlang, H.; Meyers, A.I. Tetrahedron Lett. 1993, 34, 6989-6992 and references there in.
9. See Bringmann, G.; Hartung, T. Synthesis 1992, 433-435.
10. Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375-1384.
11. Lipshutz, B.H.; Liu, Z.-P.; Kayser, F. Tetrahedron Lett. 1994, 35, 5567-5570.
12. Hayashi, T.; Kumada, M. in Asymmetric Synthesis; Morrison, J.D. Ed.; Academic Press, Inc.; 1985, vol. 5, pp. 147 and references there in.
13. Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153-8156.
14. (a) Uemura, M.; Nishimura, H.; Hayashi, T. J. Organomet. Chem. 1994, 473, 129-137.
15. (b) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101-9102.
16. (c) Kamikawa, T.; Uozumi, Y.; Hayshi, T. Tetrahedron Lett. 1996, 37, 3161-3163.
17. Suzuki, A. Pure & Appl. Chem. 1994, 66, 213-222 and references there in.
18. Stille, J.K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
19. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207-210.
20. Saá, J.M.; Martorell, G. J. Org. Chem. 1993, 58, 1963-1966.
21. For example Kawano, N.; Okigawa, M.; Hasaka, N.; Kouno, I.; Kawahara, Y.; Fujita, Y. J. Org. Chem. 1981, 46, 389-392.
22. Anderson, J.C.; Namli, H. Synlett 1995, 765-766.
23. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513-519.
24. TIOH was isolated according to George, J.H.B.; Rolfe, J.A.; Woodward, L.A. Trans. Faraday Soc. 1953, 49, 375-382.
25. Douglas, K.T.; Bunni, M.A.; Baindur, S.R. Int. J. Biochem. 1990, 22, 429.
26. (a) Uenishi, J.-I.; Bean, J.-M.; Armstrong, R.W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756-4758.
27. (b) Roush, W.R.; Brown, B.B.; Brozda, S.E. Tetrahedron Lett. 1988, 29, 3541-3544.
28. (c) Roush, W.R.; Moriarty, K.J.; Brown, B.B. Tetrahedron Lett. 1990, 31, 6509-6512.
29. (a) Hoshino, Y.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1988, 61, 3008-.3010
30. (b) Yokoe, I.; Sugita, Y.; Shirataki, Y. Chem. Pharm. Bull. 1989, 37, 529-530.
31. At 20 °C inCRC Handbook of Chemistry and Physics 77th Edition; Lide, D.R. Ed.; CRC Press; pp6-151.
32. At 25 °C in Rosenfarb, J.; Huffman, H.L.Jr.; Caruso, J.A. J. Chem. Eng. Data 1979, 21, 150-153.
33. Smith, G.B.; Dezeny, G.C.; Hughes, D.L.; King, A.O.; Verhoeven, T.R. J. Org. Chem. 1994, 59, 8151-8156.
34. Pelter, A.; Smith, K.; Brown, H.C. in Borane Reagents; Academic Press, New York; 1988.
35. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
36. Encyclopedia of Inorganic Chemistry; King, R.B., Ed.; John Wiley and Sons Ltd. 1994, vol 1, pp357.
37. Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201-2208.
38. Fu, J.-m.; Snieckus, V. Tetrahedron lett. 1990, 31, 1665-1668.
39. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J.J.; Ibers, A.J. J. Organomet. Chem. 1974, 65, 253-266.
40. Manas, M.M.; Pajeulo, F.; Pleixats, P. J. Org. Chem. 1995, 60, 2396-2397.
41. (a) Fauvarque, J.F.; Pflüger, F.; Troupel, M. J. Organometa. Chem. 1981, 208, 419-427.
42. (b) Fitton, P.; Johnson, M.P.; McKeon, J.E. J. Chem. Soc., Chem. Commun. 1968, 6-7.
43. (c) Ugo, R.: Pasini, A.; Fusi, A.; Cenini, S. J. Am. Chem. Soc. 1972, 94, 7364-7370.
44. (a) Collman, J.P.; Hegedus, L.S.; Norton, J.R.; Finke, R.G. Principles and Applications of Organotransition Metal Chemistry; University Science Books, Mill Valley, California, 1987.
45. (b) Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D.E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393-2401.
46. Stille, J.K. In The Chemistry of the Metal-Carbon Bond; Hartley, R.F.; Patai, S., Eds.; John Wiley; 1985, vol. II, pp 625-787.
47. Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033-3040.
48. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
49. Atwood, J.D. Inorganic and organometallic reaction Mechanisms; Brooks-Cole, Monterey, California, 1985.
50. Undoubtedly due to steric hindrance, see Widdowson, D.A.; Zhang, X-Z. Tetrahedron, 1986, 42, 2111-2116.
51. (a) Liebskind, L.S.; Fengl, R.W. J. Org. Chem. 1990, 55, 5359-5364.
52. (b) Gronowitz, S.; Björk, P.; Malm, J.; Hörnfeldt, A.-B. J. Organomet. Chem. 1993, 460, 127-129.
53. Still, W.C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
54. Perrin, D.D.; Armarego, W.L.F., Eds. Purification of Laboratory Chemicals, Pergamon Press, New York.
55. Coulson, D.R. Inorg. Synth. 1972, 13, 121-124.
56. Hawthorne, M.F. J. Org. Chem. 1958, 23, 1579-1580.
57. Häfelinger, G.; Hack, F.; Westermayer, G. Chem. Ber. 1978 1323-1329.