Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence

Tetrahedron

Volumn 64, Issue 22, 2008, Pages 4967-4971

  Kikuchi, Takao ^a   Nobuta, Yusuke ^a   Umeda, Junko ^a   Yamamoto, Yasunori ^a   Ishiyama, Tatsuo ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Biaryls; Boron; C H activation; Cross coupling; Pinacolborane

Indexed keywords

BORANE DERIVATIVE; BROMINE DERIVATIVE; HEXANE; PINACOLBORANE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 42749097496     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.102     Document Type: Article

References (43)

1. General reviews, see:
2. Pelter A., Smith K., and Brown H.C. Borane Reagents (1988), Academic, London
3. Vaultier M., and Carboni B. In: Abel E.W., Stone F.G.A., and Wilkinson G. (Eds). Comprehensive Organometallic Chemistry II Vol. 11 (1995), Pergamon, Oxford 191-276
4. Matteson D.S. Stereodirected Synthesis with Organoboranes (1995), Springer, Berlin
5. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457-2483
6. Li J.J., and Gribble G.W. Palladium in Heterocyclic Chemistry (2000), Elsevier, Oxford
7. Miyaura N. Top. Curr. Chem. 219 (2002) 11-59
8. A review, see:. Nesmeyanov A.N., and Sokolik R.A. Methods of Elemento-Organic Chemistry Vol. 1 (1967), North-Holland, Amsterdam
9. Reviews, see:
10. Ishiyama T., and Miyaura N. J. Synth. Org. Chem., Jpn. 57 (1999) 503-511
11. Ishiyama T., and Miyaura N. J. Organomet. Chem. 611 (2000) 392-402
12. Miyaura N. In: Togni A., and Grützmacher H. (Eds). Catalytic Heterofunctionalization (2001), Wiley-VCH, Chichester, UK Chapter 1
13. Murata M., Watanabe S., and Masuda Y. J. Org. Chem. 62 (1997) 6458-6459
14. Murata M., Oyama T., Watanabe S., and Masuda Y. J. Org. Chem. 65 (2000) 164-168
15. Chen H., and Hartwig J.F. Angew. Chem., Int. Ed. 38 (1999) 3391-3393
16. Chen H., Schlecht S., Semple T.C., and Hartwig J.F. Science 287 (2000) 1995-1997
17. Iverson C.N., and Smith III M.R. J. Am. Chem. Soc. 121 (1999) 7696-7697
18. Cho J.-Y., Iverson C.N., and Smith III M.R. J. Am. Chem. Soc. 122 (2000) 12868-12869
19. Tse M.K., Cho J.-Y., and Smith III M.R. Org. Lett. 3 (2001) 2831-2833
20. Cho J.-Y., Tse M.K., Holmes D., Maleczka Jr. R.E., and Smith III M.R. Science 295 (2002) 305-307
21. Ishiyama T., and Miyaura N. J. Organomet. Chem. 680 (2003) 3-11
22. Ishiyama T., and Miyaura N. Chem. Rec. 3 (2004) 271-280
23. Ishiyama T., Takagi J., Hartwig J.F., and Miyaura N. Angew. Chem., Int. Ed. 41 (2002) 3056-3058
24. Ishiyama T., Nobuta Y., Hartwig J.F., and Miyaura N. Chem. Commun. (2003) 2924-2925
25. Tucker C.E., Davidson J., and Knochel P. J. Org. Chem. 57 (1992) 3482-3485
26. Brown H.C., Zaidlewicz M., and Dalvi P.V. Organometallics 17 (1998) 4202-4205
27. Brown H.C., Kanth J.V., Dalvi P.V., and Zaidlewicz M. J. Org. Chem. 64 (1999) 6263-6274
28. Brown H.C., Kanth J.V.B., Dalvi P.V., and Zaidlewicz M. J. Org. Chem. 65 (2000) 4655-4661
29. Framery E., and Vaultier M. Heteroat. Chem. 11 (2000) 218-225
30. Schaeffer G.W., and Anderson E.R. J. Am. Chem. Soc. 71 (1949) 2143-2145
31. Shore S.G., and Parry R.W. J. Am. Chem. Soc. 77 (1955) 6084-6085
32. Taylor M.D., Grant L.R., and Sands C.A. J. Am. Chem. Soc. 77 (1955) 1506-1507
33. Brown H.C., Murray K.J., Murray L.J., Snover J.A., and Zweifel G. J. Am. Chem. Soc. 82 (1960) 4233-4241
34. Kanth J.V.B., and Brown H.C. Inorg. Chem. 39 (2000) 1795-1802
35. Camacho C., Uribe G., and Contreras R. Synthesis (1982) 1027-1030
36. Yamamoto Y., Miyamoto K., Umeda J., Nakatani Y., Yamamoto T., and Miyaura N. J. Organomet. Chem. 691 (2006) 4909-4917
37. Lesley G., Nguyen P., Taylor N.J., Marder T.B., Scott A.J., Clegg W., and Norman N.C. Organometallics 15 (1996) 5137-5154
38. Clegg W., Scott A.J., Dai C., Lesley G., Marder T.B., Norman N.C., and Farrugia L.J. Acta Crystallogr. C52 (1996) 2545-2547
39. Kanth J.V.B., Periasamy M., and Brown H.C. Org. Process Res. Dev. 4 (2000) 550-553
40. Shimada S., Batsanov A.S., Howard J.A.K., and Marder T.B. Angew. Chem., Int. Ed. 40 (2001) 2168-2171
41. Ishiyama T., Ishida K., Takagi J., and Miyaura N. Chem. Lett. 30 (2001) 1082-1083
42. Takagi J., Sato K., Hartwig J.F., Ishiyama T., and Miyaura N. Tetrahedron Lett. 43 (2002) 5649-5651
43. Uson R., Oro L.A., and Cabeza J.A. Inorg. Synth. 23 (1985) 126-130