C. Baillie, J. Xiao / Tetrahedron 60 (2004) 4159–4168
4167
Touati, R.; Tranchier, J. P.; Ben Hassine, B.; Genet, J. P. Adv.
Synth. Catal. 2003, 345, 261. and references cited therein.
3. Kadyrov, R.; Heinicke, J.; Kindermann, M. K.; Heller, D.;
Fischer, C.; Selke, R.; Fischer, A. K.; Jones, P. G. Chem. Ber.
1997, 130, 1663.
(400 MHz, CDCl3) d 7.76–7.72 (m, 1H), 7.41–7.16 (m,
13H), 6.96 (dd, 1H, J¼7.7, 4.2 Hz), 6.50–6.49 (m, 1H),
6.37–6.35 (m, 1H); 13C NMR (100 MHz, CDCl3) d 153.1,
142.5, 137.7 (d, JCP¼11.2 Hz), 136.6 (d, JCP¼26.4 Hz),
134.9, 134.8, 134.3 (d, JCP¼20.0 Hz), 129.1, 129.0, 128.9,
12.0 Hz); 31P NMR (162 MHz, CDCl3) d 28.3. Anal.
Calcd for C22H17PO: C, 80.47; H, 5.23. Found: C, 80.11; H,
5.2.
128.6 (d, JCP¼4.8 Hz), 127.9, 111.7, 111.0 (d, JCP
¼
4. Tsuruta, H.; Imamoto, T. Synlett 2001, 999.
5. For examples of biphenyl-based ligands in C–C coupling
reactions, see: (a) Wolfe, J. P.; Buchwald, S. L. Angew. Chem.
Int. Ed. 1999, 38, 2413. (b) Wolfe, J. P.; Singer, R. A.; Yang,
B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
(c) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am.
Chem. Soc. 2002, 124, 1162. For C–N coupling reactions, see:
(d) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem.
Soc. 1998, 120, 9722. (e) Wolfe, J. P.; Tomori, H.; Sadighi,
J. P.; Yin, J. J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
For C–O coupling reactions, see: (f) Palucki, M.; Buchwald,
S. L. J. Am. Chem. Soc. 1997, 119, 11108. (g) Ahman, J.;
Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L.
J. Am. Chem. Soc. 1998, 120, 9722. See also for preparation
methods and applications of biphenyl and related phosphines:
(h) Buchwald, S. L.; Old, D. W.; Wolfe, J. P.; Palucki, M.;
Kamikawa, K. US 6,307,087, 2001.
4.4.8. 2-(2-Diphenylphosphinophenyl)thiophene (4m).
The general procedure on a 1.1 mmol scale gave 0.29 g
1
(74% yield) of the title compound as an off-white oil. H
NMR (400 MHz, CDCl3) d 7.50–7.47 (m, 1H), 7.32–7.22
(m, 13H), 7.01 (dd, 1H, J¼7.8, 3.7 Hz), 6.93 (m, 1H), 6.85
(dd, 1H, J¼3.5, 1.3 Hz); 13C NMR (100 MHz, CDCl3) d
142.9 (d, JCP¼6.4 Hz), 140.7 (d, JCP¼28.8 Hz), 138.1 (d,
JCP¼12.0 Hz), 137.4 (d, JCP¼15.2 Hz), 134.7, 134.3 (d,
JCP¼20.0 Hz), 131.6 (d, JCP¼4.8 Hz), 128.9 (d, JCP
¼
5.6 Hz), 128.9, 128.9, 128.5 (d, JCP¼5.6 Hz), 128.3,
127.1, 126.2; 31P NMR (162 MHz, CDCl3) d 211.5.
4.4.9. 2-(2-Diphenylphosphinophenyl)pyrrole (4n). The
general procedure on a 1.2 mmol scale gave 0.29 g (75%
6. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
7. (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000,
122, 4020. (b) Hu, Q.-S.; Lu, Y.; Tang, Z. Y.; Yu, H.-B. J. Am.
Chem. Soc. 2003, 125, 2856. (c) Niyomura, O.; Tokunaga, M.;
Obora, Y.; Iwasawa, T.; Tsuji, Y. Angew. Chem. Int. Ed. 2003,
42, 1287. (d) Reid, S. M.; Boyle, R. C.; Mague, J. T.; Fink,
M. J. J. Am. Chem. Soc. 2003, 125, 7816.
1
yield) of the title compound as white crystals. H NMR
(400 MHz, CDCl3) d 8.82 (br s, 1H) 7.58–7.25 (m, 12H),
7.14 (ddd, 1H, J¼7.5, 7.5, 1.3 Hz), 6.96 (ddd, 1H, J¼7.8,
4.4, 1.3 Hz), 6.73 (m, 1H), 6.24 (m, 1H), 6.17 (m, 1H); 13C
NMR (100 MHz, CDCl3) d 137.5 (d, JCP¼10.4 Hz), 134.9,
134.3 (d, JCP¼20.0 Hz), 132.1 (d, JCP¼9.6 Hz), 130.7 (d,
JCP¼10.4 Hz), 129.7 (d, JCP¼5.6 Hz), 129.4, 129.2, 129.0
(d, JCP¼7.2 Hz), 128.8 (d, JCP¼9.6 Hz), 127.2, 118.8, 110.3
(d, JCP¼4.0 Hz), 109.5; 31P NMR (162 MHz, CDCl3) d
210.0. Anal. Calcd for C22H18PN: C, 80.71; H, 5.55; N,
4.28. Found: C, 80.48; H, 5.58; N, 4.23.
8. (a) Tomori, H.; Fox, J. M.; Buchwald, S. L. J. Org. Chem.
2000, 65, 5334. (b) Kaye, S.; Fox, J. M.; Hicks, F. A.;
Buchwald, S. L. Adv. Synth. Catal. 2001, 343, 789.
9. Baillie, C.; Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42,
9085.
10. For examples, see: (a) Slone, C. S.; Weinberger, D. A.; Mirkin,
C. A. Prog. Inorg. Chem. 1999, 48, 233. (b) Espinet, P.;
Soulantica, K. Coord. Chem. Rev. 1999, 193–195, 499.
(c) Mu¨ller, C.; Lachicotte, R. J.; Jones, W. D. Organometallics
2002, 21, 1975. (d) Kuriyama, M.; Nagai, K.; Yamada, K.;
Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124,
8932. (e) Steyer, S.; Jeunesse, C.; Matt, D.; Welter, R.;
Wesolek, M. J. Chem. Soc., Dalton Trans. 2002, 4264.
(f) Eisenberg, A. H.; Ovchinnikov, M. V.; Mirkin, C. A. J. Am.
Chem. Soc. 2003, 125, 2836.
Acknowledgements
We thank the EPSRC (C.B.) and Johnson Matthey Synetix
(J.X.) for support and Johnson Matthey for the loan of
palladium. We are also grateful to Daniele Vinci for
assistance.
11. (a) Trost, B. M.; Marschner, C. Bull. Soc. Chim. Fr. 1997, 134,
263. (b) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122,
12051. (c) Yu, H.; Hu, Q.; Pu, L. J. Am. Chem. Soc. 2000, 122,
6500. (d) Tang, W.; Chi, Y.; Zhang, X. Org. Lett. 2002, 4,
1695.
References and notes
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