Organic Letters
Letter
Commun. 2002, 32, 1401. (e) Rogers, J. F.; Green, D. M. Tetrahedron
Lett. 2002, 43, 3585.
ASSOCIATED CONTENT
Supporting Information
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*
S
(10) (a) Lossen, W. Liebigs Ann. Chem. 1869, 150, 314. (b) Lossen,
Experimental procedures and characterization data. The
W. Liebigs Ann. Chem. 1875, 175, 271. (c) Lossen, W. Liebigs Ann.
Chem. 1872, 161, 347. (d) Yale, H. L. Chem. Rev. 1943, 33, 209.
(
́
e) Bauer, L.; Exner, O. Angew. Chem. 1974, 86, 419. (f) Dube, P.;
Nathel, N. F. F.; Vetelino, M.; Couturier, M.; Aboussafy, C. L.;
Pichette, S.; Jorgensen, M. L.; Hardink, M. Org. Lett. 2009, 11, 5622.
(
(
(
(
11) Harper, S.; et al. ACS Med. Chem. Lett. 2012, 3, 332.
12) Shen, Y.; Liu, G.; Zhou, Z.; Lu, X. Org. Lett. 2013, 15, 3366.
13) For similar reactions, see: (a) Pihuleac, J.; Bauer, L. Synthesis
AUTHOR INFORMATION
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1
989, 1989, 61. (b) Jasikova, L.; Hanikyrova, E.; Skriba, A.; Jasik, J.;
Roithova, J. J. Org. Chem. 2012, 77, 2829.
*
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We thank L. C. Campeau, Kevin Campos, Zhijian Liu, and
Wensheng Yu (all at Merck) for helpful suggestions. We thank
Khateeta Emerson (Merck) for performing the gas phase IR
spectroscopy experiments.
REFERENCES
■
(
1) Tyman, J. H. P. Synthetic and Natural Phenols; Elsevier: New
York, 1996.
(
2) For selected examples of Pd-catalyzed hydroxylation, see:
(
(
a) Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912.
b) Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am.
Chem. Soc. 2006, 128, 10694. (c) Chen, G.; Chan, A. S. C.; Kwong, F.
Y. Tetrahedron Lett. 2007, 48, 473. (d) Schulz, T.; Torborg, C.;
Schaffner, B.; Huang, J.; Zapf, A.; Kadyrov, R.; Borner, A.; Beller, M.
̈ ̈
Angew. Chem., Int. Ed. 2009, 48, 918. (e) Sergeev, A. G.; Schulz, T.;
Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem.,
Int. Ed. 2009, 48, 7595. (f) Yu, C.-W.; Chen, G. S.; Huang, C.-W.;
Chern, J.-W. Org. Lett. 2012, 14, 3688. (g) Lavery, C. B.; Rotta-Loria,
N. L.; McDonald, R.; Stradiotto, M. Adv. Synth. Catal. 2013, 355, 981.
(
h) Cheung, C. W.; Buchwald, S. L. J. Org. Chem. 2014, 79, 5351.
3) For selected examples of Cu-catalyzed hydroxylation, see:
a) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int.
(
(
Ed. 2009, 48, 8725. (b) Yang, D.; Fu, H. Chem. - Eur. J. 2010, 16, 2366.
c) Zhao, D.; Wu, N.; Zhang, S.; Xi, P.; Su, X.; Lan, J.; You, J. Angew.
(
Chem., Int. Ed. 2009, 48, 8729. (d) Paul, R.; Ali, M. A.; Punniyamurthy,
T. Synthesis 2010, 2010, 4268. (e) Maurer, S.; Liu, W.; Zhang, X.;
Jiang, Y.; Ma, D. Synlett 2010, 2010, 976. (f) Chan, C.-C.; Chen, Y.-
W.; Su, C.-S.; Lin, H.-P.; Lee, C.-F. Eur. J. Org. Chem. 2011, 2011,
7
288. (g) Thakur, K. G.; Sekar, G. Chem. Commun. 2011, 47, 6692.
(
h) Xu, H.-J.; Liang, Y.-F.; Cai, Z.-Y.; Qi, H.-X.; Yang, C.-Y.; Feng, Y.
S. J. Org. Chem. 2011, 76, 2296. (i) Yang, K.; Li, Z.; Wang, Z.; Yao, Z.;
Jiang, S. Org. Lett. 2011, 13, 4340. (j) Songis, O.; Boulens, P.; Benson,
C. G. M.; Cazin, C. S. J. RSC Adv. 2012, 2, 11675. (k) Xiao, Y.; Xu, Y.;
Cheon, H.-S.; Chae, J. J. Org. Chem. 2013, 78, 5804. (l) Song, G.-L.;
Zhang, Z.; Da, Y.-X.; Wang, X.-C. Tetrahedron 2015, 71, 8823.
(
(
4) Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271.
5) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.;
Hartwig, J. F. Chem. Rev. 2010, 110, 890.
6) (a) Maleczka, R. E., Jr.; Shi, F.; Holmes, D.; Smith, M. R., III J.
(
Am. Chem. Soc. 2003, 125, 7792. (b) Fier, P. S.; Hartwig, J. F. Angew.
Chem., Int. Ed. 2013, 52, 2092.
(
7) Webb, K. S.; Levy, D. Tetrahedron Lett. 1995, 36, 5117.
(
8) Feldman, D.; Segal-Lew, D.; Rabinovitz, M. J. Org. Chem. 1991,
5
(
1
6, 7350.
9) (a) Preston, P. N.; Winwick, T. J. Chem. Soc., Perkin Trans. 1
983, 1439. (b) Showalter, H. D. H.; Johnson, J. L.; Hoftiezer, J. M. J.
Heterocycl. Chem. 1986, 23, 1491. (c) Krapcho, A. P.; Waterhouse, D.
Synth. Commun. 1998, 28, 3415. (d) Levin, J. I.; Du, M. T. Synth.
D
Org. Lett. XXXX, XXX, XXX−XXX