5
[
37]
Panja, C.; Thomas, T. E.; Gurung, L.; Rasul, G.; Mathew, T.; Olah, G.
4
.2.18. 3-(trifluoromethyl)phenol (2r).1
E
A
lu
C
en
C
t
E
p
P
et
T
ro
ED MANUSCRIPT
leu
m
A. Adv. Synth. Catal. 2009, 351, 1567-1574; (e) Chen, D.-S.; Huang, J.-
M. Synlett. 2013, 24, 499-501. (f) Kaewmati, P.; Somsook, E.; Dhital,
N. R. Sakurai, H. Tetrahedron. Lett. 2012, 53 6104-6106.
1. Xu, J.; Wang, X.; Shao, C.; Su, D.; Cheng, G.; Hu, Y. Org. Lett. 2010,
12, 1964-1967.
12. Inamoto, K.; Nozawa, K.; Yonemoto, M.; Kondo, Y. Chem. Commun.
011, 47, 11775-11777.
3. Zou, Y.-Q.; Chen, J.-R.; Liu, X.-P.; Lu, L.-Q.; Davis, R. L.; Jøgensen,
ether/ethyl acetate (15:1). Yellow oil. H NMR (CDCl , 400
MHz, ppm) 7.36(d, 2H, J = 8.0Hz), 7.20 (d, 2H, J = 8.0Hz),
.12(s, 1H), 7.04(d, 2H, J = 8.0Hz), 6.0(s, br, 1H). C NMR
3
13
7
(
1
1
1
2
CDCl , 200MHz, ppm) δ 156.0, 131.2(q, J = 64.0Hz), 130.2,
3
1 -
23.6(q, J = 542.0Hz), 118.0, 117.0, 112.3. ESI-MS [M-H] m/z
2
61.3.
1
[34]
K. A.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 784-788.
4
.2.19. naphthalen-2-ol (2s).
Eluent petroleum ether/ethyl
acetate (15:1). White solid. H NMR (CDCl , 400 MHz, ppm)
.82-7.78(m, 2H), 7.11 (d, 2H, J = 8.0Hz), 7.49-7.45(m, 1H),
.39-7.35(m, 1H), 7.18-7.13(m, 2H), 5.11(s, br, 1H). C NMR
1
14. Gawande, M. B.; Brancoa, P. S.; Varma, R. S. Chem. Soc. Rev. 2013,
2, 3371-3393.
5. Nasir Baig, R. B. ; Varma, R. S. Chem. Commun. 2013, 49, 752-770
3
4
7
7
1
13
and references therein.
(
1
CDCl , 200MHz, ppm) δ 153.2, 134.6, 129.9, 129.0, 127.8,
26.6, 126.4, 123.7, 117.4, 109.6. ESI-MS [M-H] m/z 143.3.
16. For selected examples, see: (a) Kantam, M. L.; Yadav, Y.; Laha, S.;
3
-
Srinivas, P.; Sreedhar, B.; Figueras, F. J. Org. Chem. 2009, 74, 4608-
4
2
611; (b) Kundu, D.; Chatterjee, T.; Ranu, B. C. Adv. Synth. Catal.
013, 355, 2285-2296; (c) Brahmachari, G.; Laskar, S.; Barik, P. RSC
Acknowledgements
Advances, 2013, 3, 14245-14253; (d) Parella, R.; Amit, K. N, B.;
Srinivasarao, A. Tetrahedron Lett. 2013, 54, 1738-1742; (e) Yang, S.;
Wu, C.; Zhou, H.; Yang, Y.; Zhao, Y.; Wang, C.; Yang, W.; Xu, J.,
Adv. Synth. Catal. 2013, 355, 53-58; (f) Swapna, K.; Murthy, S. N.;
Jyothi, M. T.; Nageswar, Y. V. D. Org. Biomol. Chem. 2011, 5989-
The authors wish to thank the National Natural Science
Foundation of China (Nos. 21302110, 21375075 and 21302109),
the Taishan Scholar Foundation of Shandong Province, for
financial support, the Project of Shandong Province Higher
Educational Science and Technology Program (J13LD14), the
Natural Science Foundation of Shandong Province
5
2
996; (g) Hudson, R.; Ishikawa, S.; Li, C-J.; Moores, A. Synlett. 2013,
4, 1637-1642; (h) Dandia, A.; Jain, A. K.; Sharma, S. RSC Advances,
2013, 3, 2924-2934;(i) Kumar, A. S.; Reddy, M.; Knorn, A. M.; Reiser,
O.; Sreedhar, B. Eur. J. Org. Chem. 2013, 4674-4680.
1
7. For organic synthesis in water, see: (a) Akiya, N.; Savage, P. E. Chem.
Rev. 2002, 102, 2725-2750; (b) DeSimone, J. M. Science. 2002, 297,
(ZR2013BQ017), and the Scientific Research Foundation of
Qufu Normal University (BSQD 2012021). We thank Ning
Zhang in this group for reproducing the results of 2a and 2m.
7
99-803; (c) Poliakoff, M.; Fitzpatrick, J. M.; Farren, T. R.; Anastas, P.
T. Science. 2002, 297, 807-810; (d) Teo, Y.-C.; Chua, G.-L. Chem. Eur.
J. 2009, 15, 3072-3075;(e) Meng, F.; Zhu, X.; Li, Y.; Xie, J.; Wang, B.;
Yao, J.; Wan, Y. Eur. J. Org. Chem. 2010, 6149-6152; (f) Yang, D.; Li,
B.; Yang, H.; Fu, H.; Hu, L. Synlett. 2011, 702-706; (g) Jessop, P. G.
Green Chem. 2011, 13, 1391-1398; (h) Li, X.; Yang, D.; Jiang, Y.; Fu,
H. Green Chem. 2010, 12, 1097-1105.
Supplementary Material
Supplementary data associated with this article can be found at
http:
18. Sawant, S. D.; Hudwekar, A. D.; Aravinda Kumar, K.A.;
Venkateswarlu, V.; Singh, P. P.; Vishwakarma, R. A. Tetrahedron Lett.
2
014, 55, 811-814.
9. N. Panda, A. K. Jena, S. Mohapatra, S. R. Rout, Tetrahedron Lett. 2011,
1, 1924-1927.
References and notes Ges.
1
2
5
1
2
3
4
.
.
.
.
Rappoport, Z. The Chemistry of Phenols, Wiley-VCH, Weinheim, 2003;
Hock, H.; Lang, S. Ber. Dtsch. Chem. B. 1944, 77, 257-264.
Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198
For a highlight of the palladium-catalyzed synthesis of phenols, see:
Willis, M. C.; Angew. Chem. 2007, 119, 3470-3472; Angew. Chem. Int.
Ed. 2007, 46, 3402-3404.
0. General procedure for synthesis of substituted phenols: A 25 mL
Schlenk tube equipped with a magnetic stirring bar was charged with
CuFe
arylboronic acids (1) (1.0 mmol), NaOH (3.0 mmol, 120 mg), and H
2.0 mL) was added to the tube under air atmosphere. The flask was not
2 4
O nanoparticles (0.1 mmol, 24 mg), substituted substituted
2
O
(
sealed in order that air could enter the flask, and the mixture was
allowed to stir for 24 h under air at 40 C. After completion of the
reaction, the resulting solution was cooled to room temperature, HCl
5
.
(a) Schulz,T.; Torborg, C.; Schäffner, B.; Huang, J.; Zapf, A.; Kadyrov,
R.; Börner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 918-921;
o
(b) Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am.
(
2N, 1 mL) was added to acidify the solution (pH 4-5), and the target
product was extracted with ethyl acetate (4-6 mL). The combined
organic phase was dried over anhydrous MgSO and filtered, and the
Chem. Soc. 2006, 128, 10694-10695;(c) Tlili, A.; Xia, N.; Monnier, F.;
Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725-8728; (d) Zhao, D.
B.; Wu, N. J.; Zhang, S.; Xi, P. H.; Su, X. Y.; Lan, J. B.; You, J. S.
Angew. Chem., Int. Ed. 2009, 48, 8729-8732.(e)Yang, D.; Fu, H. Chem.
Eur. J. 2010, 16, 2366-2370; (f) Yu, C. W.; Chen, G. S.; Huang, C. W.
Org. Lett. 2012, 14, 3688-3691; (g) Jia, J.; Jiang, C.; Zhang, Xi.
Tetrahedron. Lett. 2011, 52, 5593-5595;(h) Chen, J.; Yuan, T.; Hao,
W. Catal. Commu. 2011, 12, 1463-1465.(i) Yang, K.; Li, Z.; Wang, Z.
Org. Lett. 2011, 13, 4340-4343. (j) Inamoto, K.; Nozawa, K.;
Yonemoto, M. Chem. Commun. 2011, 47, 11775-11777.
4
solvent of the filtrate was removed with the aid of a rotary evaporator.
The residue was purified by column chromatography on silica gel using
petroleum ether/ethyl acetate as eluent to provide the desired product
(
2).
1. D. A. Evans, J. L. Katz, T. R. West, Tetrahedron Lett. 1998, 39, 2937-
940
2
2
2
2
2. P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs,
Tetrahedron Lett. 2003, 44, 1691-1694.
3. Pal, M.; Parasuraman, K.; Yeleswarapu, K. R. Org. Lett. 2003, 5, 349-
6
.
(a) Kleeberg, C.; Dang, L.; Lin, Z.; Marder, T. B. Angew. Chem. 2009,
1
21, 5454-5458; Angew. Chem. Int. Ed. 2009, 48, 5350-5354; (b)
Murata, M.; Oyama, T.; Watanabe, S.; Masuda, Y. J. Org. Chem. 2000,
5, 164-168; (c) Zhu, W.; Ma, D. Org. Lett. 2006, 8, 261-263; (d)
Wilson, D. A.; Wilson, C. J.; Rosen, B. M. Percec, V. Org. Lett. 2008,
0, 4879-4882.
Murata, M.; Oyama, T.; Watanabe, S.; Masuda, Y. J. Org. Chem. 2000,
5, 164-168.
Mo, F.; Jiang, Y.; Qiu, D.; Zhang, Y.; Wang, J. Angew. Chem. 2010, 49,
846-1849.
3
52.
2
2
4.
Kormos, C. M.; Leadbeater, N. E. Tetrahedron. 2006, 62, 4728-4732.
6
5. Zou, Y-Q.; Chen, J-R.; Liu, X-P.; Lu, L-Q.; Davis, R. L.; Jøgensen, K.
A.; Xiao, W-J. Angew. Chem. Int. Ed. 2012, 51, 784-788.
6. Jing, L.; Wei, J.; Zhou, L.; Huang, Z.; Lia, Z.; Zhou, X. Chem.
Commun. 2010, 46, 4767-4769.
7. Yang, D.; Fu, H. Chem. Eur. J. 2010, 16, 2366-2370.
8. Travis, B. R.; Sivakumar, M.; Olatunji Hollist, G.; Borhan, B. Org. Lett.
1
2
7
8
9
.
.
.
6
2
2
1
2
003, 5,1031-1034.
(a) Cho, J. Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E. Smith, M. R.
Science. 2002, 295, 305-308; (b) Ishiyama, T.; Takagi, J.; Ishida, K.;
Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002,
2
3
3
9. Ankner, T.; Hilmersson, G. Org. Lett. 2009, 11, 503-505.
0. Ye, Y.; Künzi, S. A.; Sanford, M. S. Org. Lett. 14, 4979-4981.
1. Inamoto, K.; Nozawa, K.; Yonemoto, M. Chem. Commun. 2011, 47,
1
24, 390-391;(c) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.;
1
1775-11777.
2. Magano, J.; Chen, M. H.; Clark, J. D.; Nussbaumer, T. J. Org. Chem.
006, 71, 7103-7105.
3. Marshall, L. J.; Cable, K. M.; Botting, N. P. Tetrahedron, 2009, 65,
165-8170.
4. Molander, G. A.; Cavalcanti, L.N. J. Org. Chem. 2011, 76, 623-630.
Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890-931.
3
3
3
1
0. (a) Brown, H.; Rao, B. C. J. Org. Chem. 1957, 22, 1136-1137; (b)
Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G.
A. J. Org. Chem. 2001, 66, 633-639; (c) Zhu, C.; Wang, R.; Falck, J. R.
Org. Lett. 2012, 14, 3494-3497; (d) Surya Prakash, G. K.; Chacko, S.;
2
8