Diastereoselective remote C-H activation by hydroboration

Chemistry - A European Journal

Volumn 10, Issue 17, 2004, Pages 4252-4264

  Varela, Jesús A ^a   Peña, Diego ^a   Goldfuss, Bernd ^b   Denisenko, Dmitri ^c   Kulhanek, Jiri ^d   Polborn, Kurt ^c   Knochel, Paul ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF COLOGNE   (Germany)

^c UNIVERSITY OF MUNICH   (Germany)

^d UNIVERSITY OF PARDUBICE   (Czech Republic)

Author keywords

C H activation; Diastereoselective 1,2 migration; Hydroboration; Organoboranes; Thermal rearrangements

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL REACTIONS; HYDROGEN BONDS; OXIDATION; SYNTHESIS (CHEMICAL);

ARYL RINGS; HYDROBORATION; THERMOLYSIS;

OLEFINS;

ALKENE DERIVATIVE; ALKENYL GROUP; BENZENE DERIVATIVE; BICYCLO COMPOUND; BIPHENYL DERIVATIVE; BORON DERIVATIVE; ETHYLENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; HYDROBORATION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 84961985310     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400023     Document Type: Article

References (71)

1. J. C. W. Lohrenz, H. Jacohsen, Angew. Chem. 1996, 108, 1403; Angew. Chem. Int. Ed. Engl. 1996, 35, 1305, and references therein.
2. J. C. W. Lohrenz, H. Jacohsen, Angew. Chem. 1996, 108, 1403; Angew. Chem. Int. Ed. Engl. 1996, 35, 1305, and references therein.
3. a) A. H. Janowicz, R. G. Bergman, J. Am. Chem. Soc. 1982, 104, 352;
4. b.) A. D. Ryabov, Chem. Rev. 1990, 90, 403;
5. c.) L. D. Field, A. V. George, B. A. Messerle, J. Chem. Soc. Chem. Commun. 1991, 1339;
6. d.) W. Adam, B. Nestler, Angew. Chem. 1993, 105, 767; Angew. Chem. Int. Ed. Engl. 1993, 32, 733;
7. d.) W. Adam, B. Nestler, Angew. Chem. 1993, 105, 767; Angew. Chem. Int. Ed. Engl. 1993, 32, 733;
8. e.) S. Murai, F. Kaikiuchi, S. Sekiine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Narure 1993. 366, 529;
9. f.) V.-G. Lim, Y. H. Kim, J. -B-Kang, J. Chem. Soc. Chem. Commun. 1994, 2267;
10. g.) F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, S. Murai, Bull. Chem. Soc. Jpn. 1995, 68, 62;
11. h.) B. A. Arndtsen, R. G. Bergman, Science 1995, 270, 1970;
12. i.) R. H. Crabtree, Chem. Rev. 1995, 95, 987;
13. j.) M. T. Rispens, C. Zardervan, B. L. Feringa, Tetrahedron: Asymmetry 1995, 6, 661;
14. k.) M. Sonoda, F. Kakiuchi, N. Chatani, S. Murai, J. Organomet. Chem. 1995, 504, 151;
15. l.) B. M. Trost, K. Iwi, I. W. Davies, J. Am. Chem. Soc. 1995, 117, 5371;
16. m.) N. A. Williams, Y. Uchimaru, M. Tanaka, J. Chem. Soc. Chem. Commun. 1995, 1129;
17. n.) P. J. Alaimo, B. A. Arndtsen, R. G. Bergman, J. Am. Chem. Soc. 1997, 119, 5269;
18. o.) R. Grigg, V. Savic, Tetrahedron Lett. 1997, 38, 5737;
19. p.) H. F. Luecke, R. G. Bergman, J. Am. Chem. Soc. 1997, 119, 11 538;
20. q.) A. Miyaluji, T. Katsuki, Tetrahedron 1998, 54, 19339;
21. r.) J. A. Johnson, D. Sames, J. Am. Chem. Soc. 2000, 122, 6321;
22. s.) H. M. L. Davies, E. G. J. Antoulinakis, J. Organomet. Chem. 2001, 617, 47;
23. t.) H. M. L. Davies, P. Ren, J. Am. Chem. Soc. 2001, 123, 2070;
24. u.) G. Dycker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698.
25. u.) G. Dycker, Angew. Chem. 1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698.
26. L. Weber in Advances in Organometallic Chemistry. Vol. 41 (Eds.: F. G. A. Stone, R. West). Academic Press, New York, 1997, pp. 1-125.
27. W. Köster, W. Siebert, Methoden der Organischen Chemie (Hauben-Weyl) 4th ed., Thieme, Stuttgart, 1952-1982, Vol. 13, Part 3a, pp. 1-908.
28. S. E. Wood, B. Rickborn, J. Org. Chem. 1983, 48, 555.
29. L. D. Field, S. P. Gallagher, Tetrahedron Lett. 1985, 26, 6125.
30. M. T. Reetz in Advances in Organometallic Chemistry, Vol. 16 (Eds.: F. G. A. Stone, R. West), Academic Press, New York, 1977, pp. 1-30.
31. F. Lhermitte, P. Knochel, Angew. Chem. 1998, 110, 2598; Angew. Chem. Int. Ed. Engl. 1998, 37, 2460.
32. F. Lhermitte, P. Knochel, Angew. Chem. 1998, 110, 2598; Angew. Chem. Int. Ed. Engl. 1998, 37, 2460.
33. H. Laaziri, L. O. Bromm, F. Lhermitte, R. M. Gschwind, P. Knochel, J. Am. Chem. Soc. 1999, 121, 6940.
34. L. O. Bromm, H. Laaziri, F. Lhermitte, K. Harms, P. Knochel, J. Am. Chem. Soc. 2000, 122, 10218.
35. J. A. Varela, D. Peña, B. Goldfuss, K. Polborn, P. Knochel, Org. Lett. 2001, 3, 2395.
36. Some remote C-H activations of organoboranes have been described; a) R. Köster, W. Larbig, G. W. Rotermund, Liehigs Ann. 1965, 682, 21;
37. b.) R. Köster, G. Rotermund, Angew. Chem. 1960, 72, 563;
38. c.) R. Köster, G. Benedikt, W. Fenzl, K. Reinert, Liebigs Ann. 1967, 702, 197.
39. For a theoretical study of the direct borane-hydrocarbon dehydrogenation, see: B. Goldfuss, P. Knochel, L. O. Bromm, K. Knapp, Angew. Chem. 2000, 112, 4302; Angew. Chem. Int. Ed. 2000, 39, 4136.
40. For a theoretical study of the direct borane-hydrocarbon dehydrogenation, see: B. Goldfuss, P. Knochel, L. O. Bromm, K. Knapp, Angew. Chem. 2000, 112, 4302; Angew. Chem. Int. Ed. 2000, 39, 4136.
41. For mechanistic studies on 1.2-boron migrations, see: a) S. E. Wood, B. Rickborn, J. Org. Chem. 1983, 48, 555;
42. b.) L. D. Field, S. P. Gallagher, Tetrahedron Lett. 1985, 26, 6125.
43. a) H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1966, 88, 1433;
44. b.) H. C. Brown, M. V. Bhatt, J. Am. Chem. Soc. 1966, 88, 1440.
45. a) M. J. S. Dewar, W. Thiel, J. Am. Chem. Soc. 1997, 119, 4907;
46. b.) M. J. S. Dewar, M. L. McKee, J. Am. Chem. Soc. 1977, 99, 5231.
47. Gaussian98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Lidshenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
48. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
49. c.) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
50. Polarized Continuum Model (PCM) and Integral Equation Formalism (IEF): a) S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117-129;
51. b.) S. Miertus, J. Tomasi, Chem. Phys. 1982, 65, 239-245;
52. c.) M. Cossi, Y. Barone, R. Cammi, J. Tomasi, Chem. Phys. Lett. 1996, 255, 327-335;
53. d.) E. Cances, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032-3041.
54. J. E. McMurry, W. J. Scott, Tetrahedron Lett. 1980, 21, 4313.
55. P. J. Stang, W. Treptow, Synthesis 1980, 283.
56. C. Ha, J. H. Horner, M. Newcomb, T. R. Varick, J. Org. Chem. 1993, 58, 1194.
57. P. J. Kropp, S. D. Crawford, J. Org. Chem. 1994, 59, 3102.
58. G. Zweifel, J. A. Miller, Org. React. 1984, 32, 430.
59. G. Cahiez, F. Lepifre, P. Ramiandrosoa, Synthesis 1999, 2138.
60. A. D. M. Curtis, A. Whiting, Tetrahedron Lett. 1991, 32, 1503.
61. O. Riant, O. Samuel, H. B. Kagan, J. Am. Chem. Soc. 1993, 115, 5835.
62. A. I. Meyers, R. J. Himmelsbach, M. Reuman, J. Org. Chem. 1983, 48, 4053.
63. B. Akermark, A. Ljungqvist, J. Organomet. Chem. 1979, 182, 47.
64. M. Virgili, J. Belloch, A. Moyano, M. A. Pericàs, A. Riera, Tetrahedron Lett. 1991, 32, 4583.
65. CCDC-161451 contains the supplementary crystallographic data for 3. These data can be obtained free of charge via www.ccdc.cam.a-c.uk/conts/retrieving. html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+ 44) 1223-336033; or deposit@ccdc.cam.uk).
66. CCDC-161450 contains the supplementary crystallographic data for 10. For further details, see ref. [31].
67. C.-G. Huang, P. Wan, J. Org. Chem. 1991, 56, 4846.
68. CCDC-213169 contains the supplementary crystallographic data for 23. For further details, see ref. [31].
69. CCDC-213168 contains the supplementary crystallographic data for 35. For further details, see ref. [31].
70. J. Almena, F. Foubelo, M. Yus, Tetrahedron 1995, 51, 3365.
71. CCDC-161449 contains the supplementary crystallographic data for 47. For further details, see ref. [31].