Edge Article
Chemical Science
3 For examples of Pd catalyzed m-C–H activation by chelation 12 (a) M. Catellani and G. P. Chiusoli, J. Organomet. Chem.,
assistance, see: (a) D. Leow, G. Li, T.-S. Mei and J.-Q. Yu,
Nature, 2012, 486, 518; (b) S. Lee, H. Lee and K. L. Tan, J.
Am. Chem. Soc., 2013, 135, 18778; (c) H.-X. Dai, G. Li,
X.-G. Zhang, A. F. Stepan and J.-Q. Yu, J. Am. Chem. Soc.,
2013, 135, 7567; (d) R.-Y. Tang, G. Li and J.-Q. Yu, Nature,
1992, 425, 151; (b) C. C. Hughes and D. Trauner, Angew.
Chem., Int. Ed., 2002, 41, 1569; (c) E. J. Hennessy and
S. L. Buchwald, J. Am. Chem. Soc., 2003, 125, 12084; (d)
B. S. Lane, M. A. Brown and D. Sames, J. Am. Chem. Soc.,
2005, 127, 8050.
2014, 507, 215; (e) M. Bera, A. Modak, T. Patra, A. Maji and 13 (a) M. Min, H. Choe and S. Hong, Asian J. Org. Chem., 2012, 1,
D. Maiti, Org. Lett., 2014, 16, 5760; (f) Y. Deng and J.-Q. Yu,
Angew. Chem., Int. Ed., 2015, 54, 888; (g) M. Bera, A. Maji,
S. K. Sahoo and D. Maiti, Angew. Chem., Int. Ed., 2015, 54,
8515; (h) S. Li, H. Ji, L. Cai and G. Li, Chem. Sci., 2015, 6, 5595.
4 For examples of p-C–H activation by chelation assistance:
47; (b) Y. Moon, D. Kwon and S. Hong, Angew. Chem., 2012,
124, 11495; (c) Experimentally, in the coupling of chromone
with benzene we observe that Pd(OPiv)2 gives 94:6 selectivity
for C2-arylation ; (d) Y. Moon and S. Hong, Chem. Commun.,
2012, 48, 7191.
S. Bag, A. Maji, A. Hazra, M. Bera and D. Maiti, J. Am. 14 B. Glover, K. A. Harvey, B. Lui, M. J. Sharp and
Chem. Soc., 2015, 137, 11888. M. F. Tymoschenko, Org. Lett., 2003, 5, 301.
5 For selected reviews on computational studies of C–H 15 (a) V. I. Sokolov, L. L. Troitskaya and O. A. Reutov, J.
activation: (a) P. E. M. Siegbahn and M. R. A. Blomberg,
Dalton Trans., 2009, 5832; (b) D. Balcells, E. Clot and
O. Eisenstein, Chem. Rev., 2010, 110, 749; (c) S. I. Gorelsky,
Coord. Chem. Rev., 2013, 257, 153; (d) Y. Boutadla,
D. L. Davies, S. A. Macgregor and A. I. Poblador-
Bahamonde, Dalton Trans., 2009, 5820.
Organomet. Chem., 1979, 182, 537; (b) A. D. Ryabov,
I. K. Sakodinskaya and A. K. Yatsimirsky, J. Chem. Soc.,
Dalton Trans., 1985, 2629; (c) M. Gomez, J. Granell and
M. Martinez, Organometallics, 1997, 16, 2539; (d)
M. Gomez, J. Granell and M. Martinez, J. Chem. Soc.,
Dalton Trans., 1998, 37; (e) B. Biswas, M. Sugimoto and
S. Sakaki, Organometallics, 2000, 19, 3895.
6 For reviews see: (a) G.-J. Cheng, X. Zhang, L. W. Chung, L. Xu
and Y.-D. Wu, J. Am. Chem. Soc., 2015, 137, 1706; (b) 16 A. Petit, J. Flygare, A. T. Miller, G. Winkel and D. H. Ess, Org.
T. Sperger, I. A. Sanhueza, I. Kalvet and F. Schoenebeck, Lett., 2012, 14, 3680.
Chem. Rev., 2015, 115, 9532 and references therein; specic 17 (a) J. C. Holder, L. Zou, A. N. Marziale, P. Liu, Y. Lan,
examples: (c) I. A. Sanhueza, A. M. Wagner, M. S. Sanford
and F. Schoenebeck, Chem. Sci., 2013, 4, 2767.
7 With pivalate: (a) M. Lafrance and K. Fagnou, J. Am. Chem.
Soc., 2006, 128, 16496; with phosphate: (b) G. Jindal and
R. B. Sunoj, J. Am. Chem. Soc., 2014, 136, 15998; (c)
G. Jindal and R. B. Sunoj, Org. Lett., 2015, 17, 2874.
M. Gatti, K. Kikushima, K. N. Houk and B. M. Stoltz, J. Am.
Chem. Soc., 2013, 135, 14996; (b) S. E. Walker, J. A. Jordan-
Hore, D. G. Johnson, S. A. Macgregor and A.-L. Lee, Angew.
Chem., Int. Ed., 2014, 53, 13876; (c) C. L. Boeser,
J. C. Holder, B. L. H. Taylor, K. N. Houk, B. M. Stoltz and
R. N. Zare, Chem. Sci., 2015, 6, 1917.
8 D. L. Davies, S. Donald and S. Macgregor, J. Am. Chem. Soc., 18 S. E. Walker, J. Boehnke, P. E. Glen, S. Levey, L. Patrick,
2005, 127, 13754. J. A. Jor-dan-Hore and A.-L. Lee, Org. Lett., 2013, 15, 1886.
9 (a) M. Lafrance and K. Fagnou, J. Am. Chem. Soc., 2006, 128, 19 (a) D. Kim and S. Hong, Org. Lett., 2011, 13, 4466; (b) M. Min,
16496; (b) M. Lafrance, C. N. Rowley, T. K. Woo and
Y. Kim and S. Hong, Chem. Commun., 2013, 49, 196; (c)
M. Min and S. Hong, Chem. Commun., 2012, 48, 9613.
´
K. Fagnou, J. Am. Chem. Soc., 2006, 128, 8754; (c) D. Garcıa-
Cuadrado, A. A. C. Braga, F. Maseras and A. M. Echavarren, 20 E. M. Simmons and J. F. Hartwig, Angew. Chem., Int. Ed.,
J. Am. Chem. Soc., 2006, 128, 1066; (d) D. Garcia-Cuadrado, 2012, 51, 3066.
P. de Mendoza, A. A. C. Braga, F. Maseras and 21 D. Wang, Y. Izawa and S. S. Stahl, J. Am. Chem. Soc., 2014,
A. M. Echavarren, J. Am. Chem. Soc., 2007, 129, 6880; (e) 136, 9914.
S. I. Gorelsky, D. Laporte and K. Fagnou, J. Am. Chem. Soc., 22 (a) T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn and
2008, 130, 10848; (f) S. I. Gorelsky, D. Lapointe and
K. Fagnou, J. Org. Chem., 2012, 77, 658; and for an overview
of mechanistic work: (g) D. Lapointe and K. Fagnou, Chem.
Lett., 2010, 39, 1118.
B. DeBoef, Org. Lett., 2007, 9, 3137; (b) N. A. B. Juwaini,
J. K. P. Ng and J. Seayad, ACS Catal., 2012, 2, 1787; (c)
S. Potavathri, K. C. Pereira, S. I. Gorelsky, A. Pike,
A. P. LeBris and B. DeBoef, J. Am. Chem. Soc., 2010, 132,
14676; (d) H. Li, J. Liu, C.-L. Sun, B.-J. Li and Z.-J. Shi, Org.
Lett., 2011, 13, 276; (e) A. N. Campbell, E. B. Meyer and
S. S. Stahl, Chem. Commun., 2011, 47, 10257; (f) C.-Y. He,
Q.-Q. Min and X. Zhang, Organometallics, 2012, 31, 1335;
(g) Z. Li, L. Ma, J. Xu, L. Kong, X. Wu and H. Yao, Chem.
Commun., 2012, 48, 3763; (h) G. Wu, J. Zhou, M. Zhang,
P. Hu and W. Su, Chem. Commun., 2012, 48, 8964; (i)
F. Chen, Z. Feng, C.-Y. He, H.-Y. Wang, Y.-L. Guo and
X. Zhang, Org. Lett., 2012, 14, 1176; (j) B. Liu, Y. Huang,
J. Lan, F. Song and J. You, Chem. Sci., 2013, 4, 2163; (k)
X. Chen, X. Huang, Q. He, Y. Xie and C. Yang, Chem.
Commun., 2014, 50, 3996.
10 (a) D. G. Musaev, A. Kaledin, B.-F. Shi and J.-Q. Yu, J. Am.
Chem. Soc., 2012, 134, 1690; (b) R. Giri, Y. Lan, P. Liu,
K. N. Houk and J.-Q. Yu, J. Am. Chem. Soc., 2012, 134,
14118; (c) M. Travis, T. M. Figg, M. Wasa, J.-Q. Yu and
D. G. Musaev, J. Am. Chem. Soc., 2013, 135, 14206; (d)
A. P. Smalley and M. J. Gaunt, J. Am. Chem. Soc., 2015, 137,
10632.
11 (a) G.-J. Cheng, Y.-F. Yang, P. Liu, P. Chen, T.-Y. Sun, G. Li,
X. Zhang, K. N. Houk, J.-Q. Yu and Y.-D. Wu, J. Am. Chem.
Soc., 2014, 136, 894; (b) Y.-F. Yang, G.-J. Cheng, P. Liu,
D. Leow, T.-Y. Sun, P. Chen, X. Zhang, J.-Q. Yu, Y.-D. Wu
and K. N. Houk, J. Am.Chem. Soc., 2014, 136, 344.
This journal is © The Royal Society of Chemistry 2016
Chem. Sci.