ACS Catalysis
Page 4 of 6
Chem. Commun. 2015, 51, 191; (r) Yamaguchi, T.; Yamaguchi, E.;
Tada, N.; Itoh, A. Adv. Synth. Catal. 2015, 357, 2017; (s) Zultanski,
S. L.; Stahl, S. S. J. Organomet. Chem. 2015, 793, 263.
(4) (a) Xu, R.; Wan, J.-P.; Mao, H.; Pan, Y. J. Am. Chem. Soc.
2010, 132, 15531; (b) Thirunavukkarasu, V. S.; Ackermann, L. Org.
Lett. 2012, 14, 6206; (c) Yang, Y.; Lin, Y.; Rao, Y. Org. Lett. 2012,
14, 2874; (d) Gallardo-Donaire, J.; Martin, R. J. Am. Chem. Soc.
2013, 135, 9350; (e) Liu, W.; Ackermann, L. Org. Lett. 2013, 15,
3484; (f) Yang, F.; Rauch, K.; Kettelhoit, K.; Ackermann, L.
Angew. Chem. Int. Ed. 2014, 53, 11285.
ASSOCIATED CONTENT
1
2
3
4
5
6
7
8
Supporting Information. Experimental procedures and
compound characterization. This material is available free of
AUTHOR INFORMATION
Corresponding Author
*E-mail: ocjg@iacs.res.in
9
(5) For some selected reviews on organic synthesis using O2 as
an oxidant, see: (a) Punniyamurthy, T.; Velusamy, S.; Iqbal, J.
Chem. Rev. 2005, 105, 2329; (b) Stahl, S. S. Science 2005, 309,
1824; (c) Muzart, J. Chem. Asian J. 2006, 1, 508; (d) Schultz, M. J.;
Sigman, M. S. Tetrahedron 2006, 62, 8227; (e) Piera, J.; Bäckvall,
J.-E. Angew. Chem. Int. Ed. 2008, 47, 3506; (f) Wendlandt, A. E.;
Suess, A. M.; Stahl, S. S. Angew. Chem. Int. Ed. 2011, 50, 11062; (g)
Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851; (h)
Wu, W.; Jiang, H. Acc. Chem. Res. 2012, 45, 1736; (i) Allen, S. E.;
Walvoord, R. R.; Padilla-Salinas, R.; Kozlowski, M. C. Chem. Rev.
2013, 113, 6234; (j) Ryland, B. L.; Stahl, S. S. Angew. Chem. Int. Ed.
2014, 53, 8824.
(6) Jintoku, T.; Nishimura, K.; Takaki, K.; Fujiwara, Y. Chem.
Lett. 1990, 19, 1687.
(7) Zhang, Y.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654.
(8) Yan, Y.; Feng, P.; Zheng, Q.-Z.; Liang, Y.-F.; Lu, J.-F.; Cui,
Y.; Jiao, N. Angew. Chem. Int. Ed. 2013, 52, 5827.
Notes
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
The authors declare no competing financial interest.
ACKNOWLEDGMENT
We gratefully acknowledge the generous financial support
received from Science and Engineering Research Board, India
(No.SB/S1/OC-52/2013) and CSIR for fellowship to PD. We.
thanks Dr. S. Chatterjee for helping with labeling experi-
ment. JG sincerely thanks Prof. B. C. Ranu and Prof. T. K.
Paine for various insightful discussions.
REFERENCES
(1) For recent reviews on palladium-catalyzed functionaliza-
tion of C-H bonds, see: (a) Negishi, E.-i. In Handbook of
Organopalladium Chemistry for Organic Synthesis; John Wiley &
Sons, Inc.: 2003, p 2783; (b) Ackermann, L.; Vicente, R.; Kapdi, A.
R. Angew. Chem. Int. Ed. 2009, 48, 9792; (c) Daugulis, O.; Do, H.-
Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074; (d) Mkhalid, I.
A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F.
Chem. Rev. 2010, 110, 890; (e) Satoh, T.; Miura, M. Chem. Eur. J.
2010, 16, 11212; (f) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem.
Soc. Rev. 2011, 40, 5068; (g) McMurray, L.; O'Hara, F.; Gaunt, M.
J. Chem. Soc. Rev. 2011, 40, 1885; (h) Wencel-Delord, J.; Droge, T.;
Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740; (i) Yeung, C. S.;
Dong, V. M. Chem. Rev. 2011, 111, 1215; (j) Engle, K. M.; Mei, T.-S.;
Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788; (k) Neufeldt, S.
R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936; (l) Yamaguchi, J.;
Yamaguchi, A. D.; Itami, K. Angew. Chem. Int. Ed. 2012, 51, 8960;
(m) Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369.
(9) (a) Stowers, K. J.; Kubota, A.; Sanford, M. S. Chem. Sci.
2012, 3, 3192; (b) Weinstein, A. B.; Stahl, S. S. Catal. Sci. Technol.
2014, 4, 4301; (c) Gerken, J. B.; Stahl, S. S. ACS Cent. Sci. 2015, 1,
234; (d) Liang, Y.-F.; Li, X.; Wang, X.; Yan, Y.; Feng, P.; Jiao, N.
ACS Catal. 2015, 5, 1956.
(10) (a) Paul, S.; Guin, J. Chem. Eur. J. 2015, 21, 17618; (b)
Biswas, P.; Paul, S.; Guin, J. Angew. Chem. Int. Ed. 2016, 55, 7756.
(11) (a) Milas, N. A. Chem. Rev. 1932, 10, 295; (b) Clinton, N. A.;
Kenley, R. A.; Traylor, T. G. J. Am. Chem. Soc. 1975, 97, 3752; (c)
Hendriks, C. F.; van Beek, H. C. A.; Heertjes, P. M. Ind. Eng.
Chem. Prod. Res. Dev. 1977, 16, 270; (d) Hendriks, C. F.; van Beek,
H. C. A.; Heertjes, P. M. Ind. Eng. Chem. Prod. Res. Dev. 1978, 17,
260; (e) Chudasama, V.; Fitzmaurice, R. J.; Caddick, S. Nat.
Chem. 2010, 2, 592; (f) Chudasama, V.; Akhbar, A. R.; Bahou, K.
A.; Fitzmaurice, R. J.; Caddick, S. Org. Biomol. Chem. 2013, 11,
7301; (g) Marteau, C.; Ruyffelaere, F.; Aubry, J. M.; Penverne, C.;
Favier, D.; Nardello-Rataj, V. Tetrahedron 2013, 69, 2268.
(12) (a) Riggio, G.; Hopff, W. H.; Hofmann, A. A.; Waser, P. G.
Helv. Chim. Acta 1983, 66, 1039; (b) Nason, D. M.; Heck, S. D.;
Bodenstein, M. S.; Lowe Iii, J. A.; Nelson, R. B.; Liston, D. R.;
Nolan, C. E.; Lanyon, L. F.; Ward, K. M.; Volkmann, R. A. Bioorg.
Med. Chem. Lett. 2004, 14, 4511; (c) Hong, F.; Hollenback, D.;
Singer, J. W.; Klein, P. Bioorg. Med. Chem. Lett. 2005, 15, 4703;
(d) Cheney, I. W.; Yan, S.; Appleby, T.; Walker, H.; Vo, T.; Yao,
N.; Hamatake, R.; Hong, Z.; Wu, J. Z. Bioorg. Med. Chem. Lett.
2007, 17, 1679.
(13) (a) Lam, F.; Xu, J. X.; Chan, K. S. J. Org. Chem. 1996, 61,
8414; (b) Kim, N. G.; Shin, C. H.; Lee, M. H.; Do, Y. J. Organomet.
Chem. 2009, 694, 1922.
(14) The reaction enabled aerobic C-H hydroxylation of azo-
compound also, delivering the corresponding ortho
hydroxylated azo-arene 2ak in 25% isolated yield under the
standard reaction conditions (see Supporting Information).
Further study towards improving the reaction efficacy of azo-
compound is our current research interest.
(2) For reviews on palladium-catalyzed C-H hydroxylation,
see: (a) Alonso, D. A.; Nájera, C.; Pastor, I. M.; Yus, M. Chem.
Eur. J. 2010, 16, 5274; (b) Enthaler, S.; Company, A. Chem. Soc.
Rev. 2011, 40, 4912.
(3) (a) Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett.
2006, 8, 1141; (b) Kim, S. H.; Lee, H. S.; Kim, S. H.; Kim, J. N.
Tetrahedron Lett. 2008, 49, 5863; (c) Wang, G.-W.; Yuan, T.-T. J.
Org. Chem. 2010, 75, 476; (d) Jiang, T.-S.; Wang, G.-W. J. Org.
Chem. 2012, 77, 9504; (e) Li, W.; Sun, P. J. Org. Chem. 2012, 77,
8362; (f) Mo, F.; Trzepkowski, L. J.; Dong, G. Angew. Chem. Int.
Ed. 2012, 51, 13075; (g) Shan, G.; Yang, X.; Ma, L.; Rao, Y. Angew.
Chem. Int. Ed. 2012, 51, 13070; (h) Zhang, S.-Y.; He, G.; Zhao, Y.;
Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134,
7313; (i) Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang,
S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 4187; (j) Choy, P. Y.; Kwong, F.
Y. Org. Lett. 2013, 15, 270; (k) Eom, D.; Jeong, Y.; Kim, Y. R.; Lee,
E.; Choi, W.; Lee, P. H. Org. Lett. 2013, 15, 5210; (l) Zhang, H.-Y.;
Yi, H.-M.; Wang, G.-W.; Yang, B.; Yang, S.-D. Org. Lett. 2013, 15,
6186; (m) Shi, S.; Kuang, C. J. Org. Chem. 2014, 79, 6105; (n)
Zhang, C.; Sun, P. J. Org. Chem. 2014, 79, 8457; (o) Dong, J.; Liu,
P.; Sun, P. J. Org. Chem. 2015, 80, 2925; (p) Liang, Y.-F.; Wang,
X.; Yuan, Y.; Liang, Y.; Li, X.; Jiao, N. ACS Catal. 2015, 5, 6148; (q)
Seth, K.; Nautiyal, M.; Purohit, P.; Parikh, N.; Chakraborti, A. K.
(15) The reaction proved to be ineffective with H2O2 or m-
CPBA. This is may be due to the fact that the oxidation of
4
ACS Paragon Plus Environment