PDF《Supporting Information》

Supporting Information for Angew.

Chem. Int. Ed. Z52419 ? Wiley-VCH

2003 69451 Weinheim, Germany page

1 The Mechanism of Bu3SnH-Mediated Homolytic Aromatic Substitution Athelstan L. J. Beckwith,* Vincent W. Bowry, W. Russell Bowman,* Emma Mann, Jonathan Parr, John M. D. Storey* Table 1. Cyclization of imidazole

12 with varying amounts of AMBN % Yield AMBN (equiv.) imidazole

16 starting material

12 2.0

88 12 1.0

92 0 0.75

80 20 0.50

43 53 0.25

8 92 0.05

0 74 [a] Bu3SnH (2.2 equiv.), AMBN and imidazole

12 in MeCN were heated under reflux,

3 h. page

2 Supporting references Reviews including reports of Bu3SnH-Mediated Homolytic Aromatic Substitution D.P. Curran, J. Sisko, P. E. Yeske, H. Liu, Pure Appl. Chem. 1993, 65, 1153-1159. I. Ryu, N. Sonoda, D.P. Curran, Chem. Rev. 1996, 96, 177-194. F. Aldabbagh, W. R. Bowman, Contemporary Org. Syn. 1997, 4, 261-280. W. R. Bowman, C. F. Bridge, P. Brookes, J. Chem. Soc., Perkin Trans.

1 2000, 1-14. W. R. Bowman, M. O. Cloonan, S. L. Krintel, J. Chem. Soc., Perkin Trans.

1 2001, 2885-2991 A. Studer, M. Bossart in Radicals in Organic Synthesis, Vol. 2, (Eds. P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, pp. 62-80. W. R. Bowman, A. J. Fletcher, G. B. S. Potts, J. Chem. Soc., Perkin Trans. 1., 2002, 2747-2762. K. C. Majumbar, P. K. Basu, Heterocycles 2002, 57, 2413-2439. page

3 Papers including reports of Bu3SnH-Mediated Homolytic Aromatic Substitution V. Martínez-Barrasa, A. G. de Viedma, C. Burgos, J. Alvarez- Builla, Organic Lett. 2000, 2, 3933-3935. A. Nunez, A. G. de Viedma, V. Martínez-Barrasa, C. Burgos, J. Alvarez-Builla, Synlett 2002, 1093-1096. A.L.J. Beckwith, J.M.D. Storey, J. Chem. Soc., Chem. Commun. 1995, 977-978. J. M. D. Storey, Tetrahedron Lett. 2000, 41, 8173-8176. M.-L. Bennasar, C. Juan, J. Bosch, Chem. Commun. 2000, 2459- 2460. M.-L. Bennasar, T. Roca, R. Griera, J. Bosch, J. Org. Chem. 2001, 66, 7547-7551. M.-L. Bennasar, T. Roca, R. Griera, M. Bassa, J. Bosch, J. Org. Chem. 2002, 67, 6268-6271. M.-L. Bennasar, E. Zulaica, C. Juan, Y. Alonso, J. Bosch, J. Org. Chem. 2002, 67, 7465-7474. W. R. Bowman, H. Heaney, B. M. Jordan, Tetrahedron 1991, 47, 10119-10128. F. Aldabbagh, W. R. Bowman, Tetrahedron Lett. 1997, 38, 3793- 3794. F. Aldabbagh, W. R. Bowman, E. Mann, Tetrahedron Lett. 1997, 38, 7937-7940. F. Aldabbagh, W. R. Bowman, Tetrahedron 1999, 55, 4109-4122. F. Aldabbagh, W. R. Bowman, E. Mann, A. M. Z. Slawin, Tetrahedron 1999, 55, 8111-8128. page

4 W. R. Bowman, E. Mann, J. Parr, J. Chem. Soc., Perkin Trans.

1 2000, 2991-2999. S. M. Allin, W. R. S. Barton, W. R. Bowman, T. McInally, Tetrahedron Lett. 2001, 42, 7887-7890. S. M. Allin, W. R. S. Barton, W. R. Bowman, T. McInally, Tetrahedron Lett. 2002, 43, 4191-4193. J. C. Estévez, M. C. Villaverde, R. J. Estévez, L. Castedo, Tetrahedron Lett. 1991, 32, 529-530. J. C. Estévez, M. C. Villaverde, R. J. Estévez, L. Castedo, Tetrahedron 1993, 49, 2783-2790. J. C. Estévez, M. C. Villaverde, R. J. Estévez, L. Castedo, Tetrahedron 1994, 50, 2107-2114. J. C. Estévez, M. C. Villaverde, R. J. Estévez, L. Castedo, Tetrahedron 1995, 51, 4075-4082. E. Martinez, J. C. Estévez, R. J. Estévez, L. Castedo, Tetrahedron 2001, 57, 1973-1979. D. Crich, J.-T. Hwang, J. Org. Chem. 1998, 63, 2765-2770. D. Crich, X.-S. Mo, J. Am. Chem. Soc. 1998, 120, 8298-8304. D. L. J. Clive, S. Kang, Tetrahedron Lett. 2000, 41, 1315- 1319. D. L. J. Clive, S. Kang, J. Org. Chem. 2001, 66, 6083-6091. A. Couture, E. Deniau, P. Grandclaudon, S. Lebrun, Synlett 1997, 1475-1477. A. Couture, E. Deniau, P. Grandclaudon, C. Hoarau, J. Org. Chem. 1998, 63, 3128-3132. C. Hoarau, A. Couture, H. Cornet, E. Deniau, P. Grandclaudon, J. Org. Chem. 2001, 66, 8064-8069. page