Organic Letters
Letter
(3) (a) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. A Very Simple
Copper-Catalyzed Synthesis of Phenols Employing Hydroxide Salts.
Angew. Chem., Int. Ed. 2009, 48, 8725−8728. (b) Zhao, D.; Wu, N.;
Zhang, S.; Xi, P.; Su, X.; Lan, J.; You, J. Synthesis of Phenol, Aromatic
Ether, and Benzofuran Derivatives by Copper-Catalyzed Hydrox-
ylation of Aryl Halides. Angew. Chem., Int. Ed. 2009, 48, 8729−8732.
(c) Maurer, S.; Liu, W.; Zhang, X.; Jiang, Y.; Ma, D. An Efficient
Synthesis of Phenol via CuI/8-Hydroxyquinoline-Catalyzed Hydrox-
ylation of Aryl Halides and Potassium Hydroxide. Synlett 2010, 2010,
976−978. (d) Paul, R.; Ali, M. A.; Punniyamurthy, T. Copper-
Catalyzed Hydroxylation of Aryl Halides with Tetrabutylammonium
Hydroxide: Synthesis of Substituted Phenols and Alkyl Aryl Ethers.
Synthesis 2010, 2010, 4268−4272. (e) Yang, D.; Fu, H. A Simple and
Practical Copper-Catalyzed Approach to Substituted Phenols from
Aryl Halides by Using Water as the Solvent. Chem. - Eur. J. 2010, 16,
2366−2370. (f) Jing, L.; Wei, J.; Zhou, L.; Huang, Z.; Li, Z.; Zhou, X.
Lithium Pipecolinate as a Facile and Efficient Ligand for Copper-
Catalyzed Hydroxylation of Aryl Halides in Water. Chem. Commun.
2010, 46, 4767−4769. (g) Yang, K.; Li, Z.; Wang, Z.; Yao, Z.; Jiang, S.
Highly Efficient Synthesis of Phenols by Copper-Catalyzed Hydrox-
ylation of Aryl Iodides, Bromides, and Chlorides. Org. Lett. 2011, 13,
4340−4343. (h) Thakur, K. G.; Sekar, G. D-Glucose as Green Ligand
for Selective Copper-Catalyzed Phenol Synthesis from Aryl Halides
with an Easy Catalyst Removal. Chem. Commun. 2011, 47, 6692−
6694. (i) Chan, C.-C.; Chen, Y.-W.; Su, C.-S.; Lin, H.-P.; Lee, C.-F.
Green Catalysts Derived from Agricultural and Industrial Waste
Products: The Preparation of Phenols from CsOH and Aryl Iodides
using CuO on Mesoporous Silica. Eur. J. Org. Chem. 2011, 2011,
7288−7293. (j) Chen, J.; Yuan, T.; Hao, W.; Cai, M. Simple and
Efficient CuI/PEG-400 System for Hydroxylation of Aryl Halides
with Potassium Hydroxide. Catal. Commun. 2011, 12, 1463−1465.
(k) Jia, J.; Jiang, C.; Zhang, X.; Jiang, Y.; Ma, D. CuI-Catalyzed
Hydroxylation of Aryl Bromides under the Assistance of 5-Bromo-2-
(1H-imidazol-2-yl)pyridine and Related Ligands. Tetrahedron Lett.
2011, 52, 5593−5595. (l) Xiao, Y.; Xu, Y.; Cheon, H.-S.; Chae, J.
Copper(II)-Catalyzed Hydroxylation of Aryl Halides Using Glycolic
acid as a Ligand. J. Org. Chem. 2013, 78, 5804−5809. (m) Cyr, P.;
Charette, A. B. Continuous-Flow Hydroxylation of Aryl Iodides
Promoted by Copper Tubing. Synlett 2014, 25, 1409−1412. (n) Ding,
G.; Han, H.; Jiang, T.; Wu, T.; Han, B. Heterogeneous Copper-
Catalyzed Hydroxylation of Aryl Iodides under Air Conditions. Chem.
Commun. 2014, 50, 9072−9075. (o) Wang, D.; Kuang, D.; Zhang, F.;
Tang, S.; Jiang, W. Triethanolamine as an Inexpensive and Efficient
Ligand for Copper-Catalyzed Hydroxylation of Aryl Halides in Water.
Eur. J. Org. Chem. 2014, 2014, 315. (p) Song, G.-L.; Zhang, Z.; Da, Y.-
X.; Wang, X.-C. Copper and L-sodium Ascorbate Catalyzed
Hydroxylation and Aryloxylation of Aryl halides. Tetrahedron 2015,
71, 8823−8829. (q) Xia, S.; Gan, L.; Wang, K.; Li, Z.; Ma, D. Copper-
Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild
Conditions. J. Am. Chem. Soc. 2016, 138, 13493−13496. (r) Zhang,
X.; Wu, G.; Gao, W.; Ding, J.; Huang, X.; Liu, M.; Wu, H. Synergistic
Photo-Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides with
Molecular Oxygen. Org. Lett. 2018, 20, 708−711.
Phosphine Ligands for Selective Palladium-Catalyzed Hydroxylation
of Aryl Halides. Angew. Chem., Int. Ed. 2009, 48, 918−921.
(e) Sergeev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.;
Neumann, H.; Beller, M. Palladium-Catalyzed Hydroxylation of Aryl
Halides under Ambient Conditions. Angew. Chem., Int. Ed. 2009, 48,
7595−7599. (f) Yu, C.-W.; Chen, G. S.; Huang, C.-W.; Chern, J.-W.
Efficient Microwave-Assisted Pd-Catalyzed Hydroxylation of Aryl
Chlorides in the Presence of Carbonate. Org. Lett. 2012, 14, 3688−
3691. (g) Lavery, C. B.; Rotta-Loria, N. L.; McDonald, R.; Stradiotto,
M. Pd2dba3/Bippyphos: A Robust Catalyst System for the
Hydroxylation of Aryl Halides with Broad Substrate Scope. Adv.
Synth. Catal. 2013, 355, 981−987. (h) Cheung, C. W.; Buchwald, S.
L. Palladium-Catalyzed Hydroxylation of Aryl and Heteroaryl Halides
Enabled by the Use of a Palladacycle Precatalyst. J. Org. Chem. 2014,
79, 5351−5358. (i) Fier, P. S.; Maloney, K. M. Synthesis of Complex
Phenols Enabled by a Rationally Designed Hydroxide Surrogate.
Angew. Chem., Int. Ed. 2017, 56, 4478−4482.
(6) Fier, P. S.; Maloney, K. M. Direct Conversion of Haloarenes to
Phenols under Mild, Transition-Metal-Free Conditions. Org. Lett.
2016, 18, 2244−2247.
(7) Fier, P. S.; Maloney, K. M. Reagent Design and Ligand Evolution
for the Development of a Mild Copper-Catalyzed Hydroxylation
Reaction. Org. Lett. 2017, 19, 3033−3036.
(8) Qiu, G.; Li, Y.; Wu, J. Recent Developments for the
Photoinduced Ar−X Bond Dissociation Reaction. Org. Chem. Front.
2016, 3, 1011−1027.
(9) (a) Li, L.; Liu, W.; Zeng, H.; Mu, X.; Cosa, G.; Mi, Z.; Li, C.-J.
Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction. J.
Am. Chem. Soc. 2015, 137, 8328−8331. (b) Yang, X.; Liu, W.; Li, L.;
Wei, W.; Li, C.-J. Photo-induced Carboiodination: A Simple Way to
Synthesize Functionalized Dihydrobenzofurans and Indolines. Chem. -
Eur. J. 2016, 22, 15252−15256.
(10) (a) Chen, K.; Cheung, M. S.; Lin, Z.; Li, P. Metal-Free
Borylation of Electron-Rich Aryl (pseudo)halides under Continuous-
Flow Photolytic Conditions. Org. Chem. Front. 2016, 3, 875−879.
(b) Mfuh, A. M.; Nguyen, V. T.; Chhetri, B.; Burch, J. E.; Doyle, J. D.;
Nesterov, V. N.; Arman, H. D.; Larionov, O. V. Additive- and Metal-
Free, Predictably 1,2- and 1,3-Regioselective, Photoinduced Dual C−
H/C−X Borylation of Haloarenes. J. Am. Chem. Soc. 2016, 138,
8408−8411.
(11) (a) Yuan, J.; To, W.-P.; Zhang, Z.-Y.; Yue, C.-D.; Meng, S.;
Chen, J.; Liu, Y.; Yu, G.-A.; Che, C.-M. Visible-Light-Promoted
Transition-Metal-Free Phosphinylation of Heteroaryl Halides in the
Presence of Potassium tert-Butoxide. Org. Lett. 2018, 20, 7816−7820.
(b) Zeng, H.; Dou, Q.; Li, C.-J. Photoinduced Transition-Metal-Free
Cross-Coupling of Aryl Halides with H-Phosphonates. Org. Lett.
2019, 21, 1301−1305.
(12) (a) Wilkinson, S. G. In Alcohols, Phenols, Ethers and Related
Compounds. In Comprehensive Organic Chemistry, The Synthesis and
Reactions of Organic Compounds; Barton, D. H. R., Ollis, W. D.,
Sutherland, I. O., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p 595.
(b) Mitsunobo, O. In Synthesis of Alcohols and Ethers. In
Comprehensive Organic Synthesis; Trost, B. N., Fleming, I., Eds.;
Pergamon Press: Oxford, 1993; Vol. 6. (c) Mulzer, J. In Synthesis of
Esters. In Comprehensive Organic Synthesis; Trost, B. N., Fleming, I.,
Eds.; Pergamon Press: Oxford, 1993; Vol. 6, p 335.
(13) Alexander, J.; Renyer, M. L.; Veerapanane, H. A Convenient
Method for the Conversion of Halides to Alcohols. Synth. Commun.
1995, 25, 3875−3881.
(14) (a) San Filippo, J.; Chern, C. I.; Valentine, J. S. Reaction of
Superoxide with Alkyl Halides and Tosylates. J. Org. Chem. 1975, 40,
1678−1680. (b) Corey, E. J.; Nicolaou, K. C.; Shibasaki, M.;
Machida, Y.; Shiner, C. S. Superoxide Ion as a Synthetically Useful
Oxygen Nucleophile. Tetrahedron Lett. 1975, 16, 3183.
(4) Yang, L.; Huang, Z.; Li, G.; Zhang, W.; Cao, R.; Wang, C.; Xiao,
J.; Xue, D. Synthesis of Phenols: Organophotoredox/Nickel Dual
Catalytic Hydroxylation of Aryl Halides with Water. Angew. Chem.,
Int. Ed. 2018, 57, 1968−1972.
(5) (a) Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L.
The Selective Reaction of Aryl Halides with KOH: Synthesis of
Phenols, Aromatic Ethers, and Benzofurans. J. Am. Chem. Soc. 2006,
128, 10694−10695. (b) Chen, G.; Chan, A. S. C.; Kwong, F. Y.
Palladium-Catalyzed C−O Bond Formation: Direct Synthesis of
Phenols and Aryl/alkyl Ethers from Activated Aryl Halides.
Tetrahedron Lett. 2007, 48, 473−476. (c) Gallon, B. J.; Kojima, R.
W.; Kaner, R. B.; Diaconescu, P. L. Palladium Nanoparticles
Supported on Polyaniline Nanofibers as a Semi-Heterogeneous
Catalyst in Water. Angew. Chem., Int. Ed. 2007, 46, 7251−7254.
(15) (a) Ito, T.; Tokuyasu, T.; Masuyama, A.; Nojima, M.;
McCullough, K. J Synthesis of Novel Macrocyclic Peroxides by
Bis(sym-collidine)iodine(I) Hexafluorophosphate-Mediated Cycliza-
tion of Unsaturated Hydroperoxides and Unsaturated Alcohols.
Tetrahedron 2003, 59, 525−536. (b) McCullough, K. J.; Tokuhara,
̈
(d) Schulz, T.; Torborg, C.; Schaffner, B.; Huang, J.; Zapf, A.;
̈
Kadyrov, R.; Borner, A.; Beller, M. Practical Imidazole-Based
E
Org. Lett. XXXX, XXX, XXX−XXX