Generation of 3-borylbenzynes, their regioselective Diels-Alder reactions, and theoretical analysis

Tetrahedron

Volumn 69, Issue 21, 2013, Pages 4338-4352

  Takagi, Akira ^a   Ikawa, Takashi ^a   Kurita, Yurio ^a   Saito, Kozumo ^a   Azechi, Kenji ^a   Egi, Masahiro ^a   Itoh, Yuji ^b   Tokiwa, Hiroaki ^b   Kita, Yasuyuki ^c,d   Akai, Shuji ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b RIKKYO UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

^d RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

Arylboronate; Aryne; Diels Alder reaction; Grignard reagent; Regioselectivity

Indexed keywords

AROMATIC COMPOUND; EPOXIDE; FURAN DERIVATIVE; PYRROLE DERIVATIVE; SULFONIC ACID DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; DIELS ALDER REACTION; OXIDATION; PRIORITY JOURNAL; STATIC ELECTRICITY; SUBSTITUTION REACTION; THEORETICAL STUDY;

ALNUS;

EID: 84876283686     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.03.016     Document Type: Article

References (68)

1. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457 2483
2. F. Monnier, and M. Taillefer Angew. Chem., Int. Ed. 48 2009 6954 6971
3. S. Shinkai, and M. Takeuchi Biosens. Bioelectron. 20 2004 1250 1259
4. S.A. Elfeky, S.E. Flower, N. Masumoto, F. D'Hooge, L. Labarthe, W. Chen, C. Len, T.D. James, and J.S. Fossey Chem. - Asian J. 5 2010 581 588
5. S.J. Baker, Y.-K. Zhang, T. Akama, A. Lau, H. Zhou, V. Hernandez, W. Mao, M.R.K. Alley, V. Sanders, and J.J. Plattner J. Med. Chem. 49 2006 4447 4450
6. B.D. Dorsey, M. Iqbal, S. Chatterjee, E. Menta, R. Bernardini, A. Bernareggi, P.G. Cassarà, G. D'Arasmo, E. Ferretti, S. De Munari, A. Oliva, G. Pezzoni, C. Allievi, I. Strepponi, B. Ruggeri, M.A. Ator, M. Willliams, and J.P. Mallamo J. Med. Chem. 51 2008 1068 1072
7. R.F. Barth, A.H. Soloway, R.G. Fairchild, and R.M. Brugger Cancer 70 1992 2995 3007
8. R.F. Barth, J.A. Coderre, M.G.H. Vicente, and T.E. Blue Clin. Cancer Res. 11 2005 3987 4002
9. T. Ishiyama, K. Ishida, and N. Miyaura Tetrahedron 57 2001 9813 9816
10. E. Tyrrell, and P. Brookes Synthesis 2003 469 483
11. T.A. Boebel, and J.F. Hartwig J. Am. Chem. Soc. 130 2008 7534 7535
12. Y. Yamamoto, K. Hattori, J. Ishii, and H. Nishiyama Tetrahedron 62 2006 4294 4305
13. J. Huang, S.J.F. Macdonald, and J.P.A. Harrity Chem. Commun. 2009 436 438
14. J.D. Kirkham, R.J. Butlin, and J.P.A. Harrity Angew. Chem., Int. Ed. 51 2012 6402 6405
15. J.D. Kirkham, A.G. Leach, E.C. Row, and J.P.A. Harrity Synthesis 2012 1964 1973
16. H.H. Wenk, M. Winkler, and W. Sander Angew. Chem., Int. Ed. 42 2003 502 528
17. S.A. Worlikar, and R.C. Larock Curr. Org. Chem. 15 2011 3214 3232
18. A. Bhunia, S.R. Yetra, and A.T. Biju Chem. Soc. Rev. 41 2012 3140 3152
19. P.M. Tadross, and B.M. Stoltz Chem. Rev. 112 2012 3550 3577
20. W.M. Best, and D. Wege Tetrahedron Lett. 22 1981 4877 4880
21. G.W. Gribble, M.G. Saulnier, M.P. Sibi, and J.A. Obaza-Nutaitis J. Org. Chem. 49 1984 4518 4523
22. T. Matsumoto, T. Hosoya, and K. Suzuki J. Am. Chem. Soc. 114 1992 3568 3570
23. T. Hosoya, E. Takashiro, T. Matsumoto, and K. Suzuki J. Am. Chem. Soc. 116 1994 1004 1015
24. T. Matsumoto, T. Sohma, H. Yamaguchi, S. Kurata, and K. Suzuki Tetrahedron 51 1995 7347 7360
25. C.-L. Chen, S.M. Sparks, and S.F. Martin J. Am. Chem. Soc. 128 2006 13696 13697
26. M.S. Newman, and R. Kannan J. Org. Chem. 41 1976 3356 3359
27. K. Shankaran, and V. Snieckus Tetrahedron Lett. 25 1984 2827 2830
28. T. Nishiyama, M. Okada, and M. Miyazawa Reports of Kyushu School of Engineering, Kinki University 28 2000 37 43
29. J.E. Anderson, R.W. Franck, and W.L. Mandella J. Am. Chem. Soc. 94 1972 4608 4614
30. G.W. Gribble, D.J. Keavy, S.E. Branzt, W.J. Kelly, and M.A. Pals Tetrahedron Lett. 29 1988 6227 6230
31. R.G.F. Giles, A.B. Hughes, and M.V. Sargent J. Chem. Soc., Perkin Trans. 1 1991 1581 1587
32. S. Akai, T. Ikawa, S. Takayanagi, Y. Morikawa, S. Mohri, M. Tsuabkiyama, M. Egi, Y. Wada, and Y. Kita Angew. Chem., Int. Ed. 47 2008 7673 7676
33. J.E. Huheey Inorganic Chemistry 1983 Harper & Row New York, NY
34. T. Ikawa, A. Takagi, Y. Kurita, K. Saito, K. Azechi, M. Egi, K. Kakiguchi, Y. Kita, and S. Akai Angew. Chem., Int. Ed. 49 2010 5563 5566
35. A part of this work was also briefly reported in our very recent review article, see: T. Ikawa, H. Tokiwa, and S. Akai J. Synth. Org. Chem., Jpn. 70 2012 1123 1133
36. T. Matsumoto, T. Hosoya, M. Katsuki, and K. Suzuki Tetrahedron Lett. 32 1991 6735 6736
37. Y. Himeshima, T. Sonoda, and H. Kobayashi Chem. Lett. 1983 1211 1214
38. I. Sapountzis, W. Lin, M. Fischer, and P. Knochel Angew. Chem., Int. Ed. 43 2004 4364 4366
39. W. Lin, L. Chen, and P. Knochel Tetrahedron 63 2007 2787 2797
40. M.J. Fleming, H.A. McManus, A. Rudolph, W.H. Chan, J. Ruiz, C. Dockendorff, and M. Lautens Chem. - Eur. J. 14 2008 2112 2124
41. C. Dockendorff, S. Jin, M. Olsen, M. Lautens, M. Coupal, L. Hodzic, N. Spear, K. Payza, C. Walpole, and M.J. Tomaszewski Bioorg. Med. Chem. Lett. 19 2009 1228 1232
42. G.W. Gribble, and W.J. Kelly Tetrahedron Lett. 26 1985 3779 3782
43. C.C. Tzschucke, J.M. Murphy, and J.F. Hartwig Org. Lett. 9 2007 761 764
44. H.-X. Dai, and J.-Q. Yu J. Am. Chem. Soc. 134 2012 134 137
45. M.M. Hussain, and P.J. Walsh Angew. Chem., Int. Ed. 49 2010 1834 1837
46. M. Lautens, S. Hiebert, and J.-L. Renaud J. Am. Chem. Soc. 123 2001 6834 6839
47. T.E. Barder, S.D. Walker, J.R. Martinelli, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 4685 4696
48. H.G. Kuivila, and K.V. Nahabedian J. Am. Chem. Soc. 83 1961 2159 2163
49. D.C. Roberts, K. Suda, J. Samanen, and D.S. Kemp Tetrahedron Lett. 21 1980 3435 3438
50. H.C. Brown, and G.A. Molander J. Org. Chem. 51 1986 4512 4514
51. T. Hamura, Y. Ibusuki, K. Sato, T. Matsumoto, Y. Osamura, and K. Suzuki Org. Lett. 5 2003 3551 3554
52. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision B.01 2010 Gaussian Wallingford CT
53. K.B. Wiberg Tetrahedron 24 1968 1083 1096
54. J.P. Foster, and F. Weinhold J. Am. Chem. Soc. 102 1980 7211 7218
55. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735 746
56. E.D. Glendening, J.K. Badenhoop, A.E. Reed, J.E. Carpenter, J.A. Bohmann, C.M. Morales, and F. Weinhold NBO5 2001 Theoretical Chemistry Institute, University of Wisconsin Madison, USA
57. D.H. Ess, and K.N. Houk J. Am. Chem. Soc. 129 2007 10646 10647
58. P.H.-Y. Cheong, R.S. Paton, S.M. Bronner, G.-Y.J. Im, and K.N. Houk J. Am. Chem. Soc. 132 2010 1267 1269
59. S.M. Bronner, J.L. Mackey, K.N. Houk, and N.K. Garg J. Am. Chem. Soc. 134 2012 13966 13969
60. P.C. Bélanger, and C. Dufresne Can. J. Chem. 64 1986 1514 1520
61. P.-L. Wu, M. Chu, and F.W. Fowler J. Org. Chem. 53 1988 963 972
62. A.G. Lohse, E.H. Krenske, J.E. Antoline, K.N. Houk, and R.P. Hsung Org. Lett. 12 2010 5506 5509
63. N. Sofikiti, M. Tofi, T. Montagnon, G. Vassilikogiannakis, and M. Stratakis Org. Lett. 7 2005 2357 2359
64. M. Egi, K. Azechi, and S. Akai Org. Lett. 11 2009 5002 5005
65. W. Chen, E.K. Stephenson, M.P. Cava, and Y.A. Jackson Org. Synth. 70 1992 151 153
66. M. Kauch, and D. Hoppe Synthesis 2006 1578 1589
67. T. Kometani, D.S. Watt, T. Ji, and T. Fitz J. Org. Chem. 50 1985 5384 5387
68. W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2923 2925