W. Zhang, T. Nagashima / Journal of Fluorine Chemistry 127 (2006) 588–591
591
[2] Selected reviews:
(d) J. Zhu, A. Bigot, M.E. Tran Huu Dau, Tetrahedron Lett. 38 (1997)
1181.
(a) S. Brase, J.H. Kirchhoff, J. Kobberling, Tetrahedron 59 (2003) 885;
(b) B.A. Lorsbach, M.J. Kurth, Chem. Rev. 99 (1999) 1549.
[3] (a) W. Zhang, Chem. Rev. 104 (2004) 2531;
(b) W. Zhang, Curr. Opin. Drug Disc. Dev. 7 (2004) 784;
(c) W. Zhang, Tetrahedron 59 (2003) 4475;
[8] L.N. Pridgen, G.K. Huang, Tetrahedron Lett. 39 (1998) 8421.
[9] General procedures for the preparation of aryl perfluorooctanesulfonates
1: to a mixture of phenol (20.0 mmol) and K2CO3 (21.0 mmol) in DMF
(15 mL) was added perfluorooctanesulfonyl fluoride (16.7 mmol) drop-
wise through an addition funnel. After heating at 70 8C for 5 h, the mixture
was poured into water (100 mL), and was extracted with ethyl acetate. The
organic layer was dried over MgSO4, and the solvent was evaporated
under vacuum to give aryl perfluorooctanesulfonate 1 in 85–90% yields.
The crude product was used for the next step reaction. If needed, the crude
product could be further purified by recrystallization from MeOH or by F-
SPE.
(d) W. Zhang, in: J.A. Gladysz, D.P. Curran, I.T. Horvath (Eds.), Hand-
book of Fluorous Chemistry, Wiley–VCH, Weinheim, 2004, pp. 222–236.
[4] (a) W. Zhang, C.H.-T. Chen, Y. Lu, T. Nagashima, Org. Lett. 6 (2004)
1473;
(b) W. Zhang, T. Nagashima, Y. Lu, C.H.-T. Chen, Tetrahedron Lett. 45
(2004) 4611;
(c) Y. Lu, W. Zhang, QSAR Comb. Sci. 23 (2004) 827;
(d) W. Zhang, Y. Lu, C.H.-T. Chen, Mol. Divers. 7 (2003) 199.
[5] (a) K.W. Anderson, M. Mendez-Perez, J. Priego, S.L. Buchwald, J. Org.
Chem. 68 (2003) 9563;
[10] FluoroFlash SPE cartridges are packed with silica gel with a stationary
phase of Si(Me)2CH2CH2C8F17. They are commercially available from
(b) J.P. Wolfe, H. Tomori, J.P. Sadighi, J. Yin, S.L. Buchwald, J. Org.
Chem. 65 (2000) 1158;
[11] J. Ahman, S.L. Buchwald, Tetrahedron Lett. 38 (1997) 6363.
[12] General procedures for cross-coupling reactions of aryl perfluoroocta-
nesulfonates with amines: fluorous sulfonate 1b (0.129 g, 0.205 mmol),
Pd(OAc)2 (6 mg, 0.03 mmol), BINAP (22 mg, 0.04 mmol), and Cs2CO3
(95 mg, 0.29 mmol) were added to a flask under an nitrogen atmo-
sphere. Benzylamine (46 mg, 0.43 mmol) in toluene (3 mL) was
added. The mixture was stirred at 90 8C for 48 h. After cooling, the
reaction mixture was directly loaded to a silica gel column, eluted
with 3:1 hexanes/EtOAc to give product (29.3 mg, 0.13 mmol) in 61%
yield.
(c) I.L. Baraznenok, V.G. Nenajdenko, E.S. Balenkova, Tetrahedron 56
(2000) 3077;
(d) K. Ritter, Synthesis (1993) 735;
(e) W.J. Scott, J.E. McMurry, Acc. Chem. Res. 21 (1988) 47;
(f) P.J. Stang, M. Hanack, L.R. Subrmanian, Synthesis (1982) 85.
[6] (a) Y. Pan, C.P. Holmes, Org. Lett. 3 (2001) 2769;
(b) Y. Pan, B. Ruhland, C.P. Holmes, Angew. Chem. Int. Ed. 40 (2001)
4488;
For other polymer-supported arylsulfonate linkers, see
(c) C.-H. Cho, H. Park, M.-A. Park, T.-Y. Ryoo, Y.-S. Lee, K. Park, Eur. J.
Org. Chem. (2005) 3177;
[13] J. Louie, M.S. Driver, B.C. Hamann, J.F. Hartwig, J. Org. Chem. 62 (1997)
1268.
[14] Analytical data for compound 6: 1H NMR (270 MHz, CDCl3): d 8.73 (2H,
dd, J = 2.3, 8.0 Hz), 8.26 (2H, d, J = 8.9 Hz), 8.19 (2H, d, J = 8.7 Hz), 7.83
(1H, s), 7.60–7.45 (3H, m), 7.44–7.28 (5H, m), 7.07 (2H, d, J = 8.8 Hz),
6.76 (2H, d, J = 8.7 Hz), 4.43 (3H, broad s), 3.91 (3H, s). 13C NMR
(67.5 MHz, CDCl3): d 164.2, 164.0, 163.5, 161.6, 150.3, 138.8, 138.7,
130.4, 128.8, 128.7, 128.4, 127.5, 126.4, 114.1, 112.6, 107.8, 55.5, 47.9.
LRMS (APCI) m/z 444.2 [M + H]+.
(d) A.N. Cammidge, Z. Ngaini, Chem. Commun. (2004) 1914;
(e) J.D. Revell, A. Ganesan, Chem. Commun. (2004) 1916.
[7] (a) X. Zhang, Z. Sui, Tetrahedron Lett. 44 (2003) 3071;
(b) V.V. Grushin, Organomettallics 19 (2000) 1888;
(c) L. Neuville, A. Bigot, M.E. Tran Huu Dau, J. Zhu, J. Org. Chem. 64
(1999) 7638;