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171. (a) S. D. Walker, T. E. Barder, J. R. Martinelli and S. L. Buchwald, Angew.
Chem. Int. Ed., 2004, 43, 1871. For a more detailed study, see:
(b) T. E. Barder, S. D. Walker, J. R. Martinelli and S. L. Buchwald, J. Am.
Chem. Soc., 2005, 127, 4685.
172. Pd(0)-arene interactions had been previously observed in related
complexes: (a) J. Yin, M. P. Rainka, X.-X. Zhang and S. L. Buchwald,
J. Am. Chem. Soc., 2002, 124, 1162; (b) S. M. Reid, R. C. Boyle,
J. T. Mague and M. J. Fink, J. Am. Chem. Soc., 2003, 125, 7816.
173. Representative examples: Refs 158a and 167 and (a) K. L. Billingsley,
K. W. Anderson and S. L. Buchwald, Angew. Chem. Int. Ed., 2006,
45, 3484; (b) A. Metzger, L. Melzig and P. Knochel, Synthesis, 2010,
2853; (c) Q. Tang and R. Gianatassio, Tetrahedron Lett., 2010, 51, 3473.
Also see Ref. 158f and references therein.
174. Examples: Ref. 165c and (a) R. C. Hodgkinson, J. Schulz and
M. C. Willis, Tetrahedron, 2009, 65, 8940; (b) F. Perez and A. Minatti,
Org. Lett., 2011, 13, 1984.
175. J. E. Milne and S. L. Buchwald, J. Am. Chem. Soc., 2004, 126, 13028.
176. E. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watson and
S. L. Buchwald, Science, 2010, 328, 1679.
177. (a) D. A. Watson, M. Su, G. Teverovskiy, Y. Zhang, J. Garc´a-Fortanet,
T. Kinzel and S. L. Buchwald, Science, 2009, 325, 1661; (b) T. No¨l,
T. J. Maimone and S. L. Buchwald, Angew. Chem. Int. Ed., 2011,
50, 8900; (c) T. J. Maimone, P. J. Milner, T. Kinzel, Y. Zhang,
M. K. Takase and S. L. Buchwald, J. Am. Chem. Soc., 2011, 133, 18106;
(d) H. G. Lee, P. J. Milner and S. L. Buchwald, Org. Lett., 2013, 15, 5602.
For the use of a teraryl phosphine ligand in Pd-catalyzed aryl fluorin-
ation, see (e) H. G. Lee, P. J. Milner and S. L. Buchwald, J. Am. Chem.
Soc., 2014, 136, 3792.
178. G. Teverovskiy, D. S. Surry and S. L. Buchwald, Angew. Chem. Int. Ed.,
2011, 50, 7312.
179. Cyanate: (a) E. V. Vinogradova, B. P. Fors and S. L. Buchwald, J. Am.
Chem. Soc., 2012, 134, 11132; (b) E. V. Vinogradova, N. H. Park,
B. P. Fors and S. L. Buchwald, Org. Lett., 2013, 15, 13942-Aminothia-
zoles: (c) M. A. McGowan, J. L. Henderson and S. L. Buchwald, Org.
Lett., 2012, 14, 1432. Amidines: (d) M. A. McGowan, C. Z. McAvoy and
S. L. Buchwald, Org. Lett., 2012, 14, 3800. Alcohols: Refs 159a-c Halo-
gens (not F): (e) J. Pan, X. Wang, Y. Zhang and S. L. Buchwald, Org. Lett.,
2011, 13, 4974.
180. (a) R. A. Singer, M. Dor´, J. E. Sieser and M. A. Berliner, Tetrahedron
Lett., 2006, 47, 3727; (b) G. J. Withbroe, R. A. Singer and J. E. Sieser, Org.
Process Res. Dev., 2008, 12, 480; (c) S. Gowrisankar, A. G. Sergeev,
P. Anbarasan, A. Spannenberg, H. Neumann and M. Beller, J. Am.
Chem. Soc., 2010, 132, 11592; (d) A. Porzelle, M. D. Woodrow and
N. C. O. Tomkinson, Org. Lett., 2009, 11, 233; (e) B. J. Kotecki, D. P.
Fernando, A. R. Haight and K. A. Lukin, Org. Lett., 2009, 11,
947; (f) F. Rataboul, A. Zapf, R. Jackstell, S. Harkal, T. Riermeier,
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