Abstract
We explored the most expedient pathway for phenolic compound preparation using a combination of arylboronic acids, a green oxidant (H2O2) and a catalytic amount of readily available medicinal materials (TYLENOL® and ASPIRIN®). The arylboronic acids were successfully transformed into the corresponding phenols in high yields under metal- and base-free aqueous aerobic conditions. We demonstrated that enhanced availability and sustainability are some advantages associated with the use of medicinal supports.
Keywords: TYLENOL®, ASPIRIN®, green promoters, ipso-hydroxylation, arylboronic acids, phenols.
Graphical Abstract
[1]
(a)Synthetic and Natural Phenols; Elsevier: New York, 1996.
(b)Rappoport, Z. The Chemistry of Phenols; Wiley-VCH: Weinheim, 2003.
(b)Rappoport, Z. The Chemistry of Phenols; Wiley-VCH: Weinheim, 2003.
[2]
(a)Hoarau, C.; Pettus, T.R.R. Synlett, 2003, 127.
(b)Hanson, P.; Jones, J.R.; Taylor, A.B.; Walton, P.H.; Timms, A.W. J. Chem. Soc., Perkin Trans. 2, 2002, 1135.
(c)George, T.; Mabon, R.; Sweeney, G.; Sweeney, B.J.; Tavassoli, A. J. Chem. Soc., Perkin Trans. 1, 2000, 2529.
(d)Thakur, K.G.; Sekar, G. Chem. Commun. (Camb.), 2011, 6692.
(e)Mehmood, A.; Leadbeater, N.E. Catal. Commun., 2010, 12, 64.
(b)Hanson, P.; Jones, J.R.; Taylor, A.B.; Walton, P.H.; Timms, A.W. J. Chem. Soc., Perkin Trans. 2, 2002, 1135.
(c)George, T.; Mabon, R.; Sweeney, G.; Sweeney, B.J.; Tavassoli, A. J. Chem. Soc., Perkin Trans. 1, 2000, 2529.
(d)Thakur, K.G.; Sekar, G. Chem. Commun. (Camb.), 2011, 6692.
(e)Mehmood, A.; Leadbeater, N.E. Catal. Commun., 2010, 12, 64.
[3]
Zhu, C.; Wang., R.; Falck, J. R. Org. Lett., 2012, 14, 3494.
[http://dx.doi.org/10.1021/ol301463c] [PMID: 22731862]
[http://dx.doi.org/10.1021/ol301463c] [PMID: 22731862]
[4]
(a)Molander, G.A.; Cavalcanti, L.N. J. Org. Chem., 2011, 76, 623.
[http://dx.doi.org/10.1021/jo102208d]
(b)Maleczka, R.E., Jr; Shi, F.; Holmes, D.; Smith, III. M.R. J. Am. Chem. Soc., 2003, 125, 7792.
(c)Travis, B.R.; Ciaramitaro, B.P.; Borhan, B. Eur. J. Org. Chem., 2002, 3429.
(d)Webb, K.S.; Levy, D. Tetrahedron Lett., 1995, 36, 5117.
[http://dx.doi.org/10.1016/00404-0399(50)0963D-]
[http://dx.doi.org/10.1021/jo102208d]
(b)Maleczka, R.E., Jr; Shi, F.; Holmes, D.; Smith, III. M.R. J. Am. Chem. Soc., 2003, 125, 7792.
(c)Travis, B.R.; Ciaramitaro, B.P.; Borhan, B. Eur. J. Org. Chem., 2002, 3429.
(d)Webb, K.S.; Levy, D. Tetrahedron Lett., 1995, 36, 5117.
[http://dx.doi.org/10.1016/00404-0399(50)0963D-]
[5]
Chatterjee, N.; Goswami, A. Tetrahedron Lett., 2015, 56, 1524.
[http://dx.doi.org/10.1016/j.tetlet.2015.01.118]
[http://dx.doi.org/10.1016/j.tetlet.2015.01.118]
[6]
Kianmehr, E.; Yahyaee, M. Tabatabai. K. Tetrahedron Lett., 2007, 48, 2713.
[http://dx.doi.org/10.1016/j.tetlet.2007.02.069]
[http://dx.doi.org/10.1016/j.tetlet.2007.02.069]
[7]
(a)Guo, S.; Lu, L.; Cai, H. Synlett, 2014, 24, 1712.
[http://dx.doi.org/10.1055/s-0033-1339303]
(b)Chen, D.S.; Huang, J.M. Synlett, 2013, 24, 499.
[http://dx.doi.org/10.1055/s-0033-1339303]
(b)Chen, D.S.; Huang, J.M. Synlett, 2013, 24, 499.
[8]
(a)Dar, B.A.; Bhatti, P.; Singh, A.P.; Lazar, A.; Sharma, P.R.; Sharma, M.; Singh, B. Appl. Catal. A., 2013, 466, 60.
(b)Yang, D.; An, B.; Wei, W.; Jiang, M.; You, J.; Wang, H. Tetrahedron, 2014, 70, 3630.
(c)Yang, H.; Li, Y.; Jiang, M.; Wang, J.; Fu, H. Chemistry, 2011, 17, 5652.
(d)Affrose, A.; Azath, I.A.; Dhakshinamoorthy, A.; Pitchumani, K. J. Mol. Catal. Chem., 2014, 395, 500.
(e)Xu, J.; Wang, X.; Shao, C.; Su, D.; Cheng, G.; Hu, Y. Org. Lett., 2010, 12, 1964.
(f)Inamoto, K.; Nozawa, K.; Yonemoto, M.; Kondo, Y. Chem. Commun. (Camb.), 2011, 47, 11775.
(g)Zheng, J.; Lin, S.; Zhu, X.; Jiang, B.; Yang, Z. Pan. Z. Chem. Commun., 2012, 48, 6235.
(h)Gogoi, N.; Gogoi, P.K.; Borah, G.; Bora, U. Tetrahedron Lett., 2016, 57, 4050.
(i)Silveria, D.G.; Monzon, D.M.; Crisostomo, F.P.; Martin, T.; Martin, V.S.; Carrillo, R. Chem. Commun. (Camb.), 2015, 51, 7027.
(b)Yang, D.; An, B.; Wei, W.; Jiang, M.; You, J.; Wang, H. Tetrahedron, 2014, 70, 3630.
(c)Yang, H.; Li, Y.; Jiang, M.; Wang, J.; Fu, H. Chemistry, 2011, 17, 5652.
(d)Affrose, A.; Azath, I.A.; Dhakshinamoorthy, A.; Pitchumani, K. J. Mol. Catal. Chem., 2014, 395, 500.
(e)Xu, J.; Wang, X.; Shao, C.; Su, D.; Cheng, G.; Hu, Y. Org. Lett., 2010, 12, 1964.
(f)Inamoto, K.; Nozawa, K.; Yonemoto, M.; Kondo, Y. Chem. Commun. (Camb.), 2011, 47, 11775.
(g)Zheng, J.; Lin, S.; Zhu, X.; Jiang, B.; Yang, Z. Pan. Z. Chem. Commun., 2012, 48, 6235.
(h)Gogoi, N.; Gogoi, P.K.; Borah, G.; Bora, U. Tetrahedron Lett., 2016, 57, 4050.
(i)Silveria, D.G.; Monzon, D.M.; Crisostomo, F.P.; Martin, T.; Martin, V.S.; Carrillo, R. Chem. Commun. (Camb.), 2015, 51, 7027.
[9]
(a)Sawant, S.D.; Hudweker, A.D.; Kumar, K.A.A.; Venkateswarlu, V.; Singh, P.P.; Vishwakarma, R.A. Tetrahedron Lett., 2014, 55, 811.
[http://dx.doi.org/10.1016/j.tetlet.2013.12.003]
(b)Wang, Z.J.; Li, R.; Landfester, K.; Zhang, K.A.I. Polymer (Guildf.), 2017, 126, 291.
[http://dx.doi.org/10.1016/j.polymer.2017.04.052]
[http://dx.doi.org/10.1016/j.tetlet.2013.12.003]
(b)Wang, Z.J.; Li, R.; Landfester, K.; Zhang, K.A.I. Polymer (Guildf.), 2017, 126, 291.
[http://dx.doi.org/10.1016/j.polymer.2017.04.052]
[10]
(a)Zhong, Y.; Yuan, L.; Huang, Z.; Gu, W.; Shao, Y.; Han, W. RSC Adv., 2014, 4, 33164.
[http://dx.doi.org/10.1039/C4RA05589F]
(b)Kotoučová, H.; Strnadová, I.; Kovandová, M.; Chudoba, J.; Dvořákovác, H.; Cibulka, R. Org. Biom. Chem., 2014, 12, 2137.
[http://dx.doi.org/10.1039/C4RA05589F]
(b)Kotoučová, H.; Strnadová, I.; Kovandová, M.; Chudoba, J.; Dvořákovác, H.; Cibulka, R. Org. Biom. Chem., 2014, 12, 2137.
[11]
Laskar, K.; Paul, S.; Bora, U. Tetrahedron Lett., 2019, 60, 151044.
[http://dx.doi.org/10.1016/j.tetlet.2019.151044]
[http://dx.doi.org/10.1016/j.tetlet.2019.151044]
[12]
(a)Gupta, S.; Chaudhary, P.; Srivastava, V.; Kandasamy, J. Tetrahedron Lett., 2016, 57, 2506.
(b)Mahanta, A.; Adhikari, P.; Bora, U.; Thakur, A.J. Tetrahedron Lett., 2015, 56, 1780.
(c)Gogoi, K.; Dewan, A.; Gogoi, A.; Borah, G.; Bora, U. Heteroatom Chem., 2014, 25, 127.
(d)Gogoi, A.; Bora, U. Tetrahedron Lett., 2013, 54, 1821.
(e)Saikia, E.; Bora, S.J.; Chetia, B. RSC. Adv., 2015, 5, 102723.
(f)Prakash, G.K.S.; Chacko, S.; Panja, C.; Thomas, T.E.; Gurung, L.; Rasul, G.; Mathew, T.; Olah, G.A. Adv. Synth. Catal., 2009, 351, 1567.
(g)Gogoi, A. Bora. U. Synlett, 2012, 23, 1079.
(h)Mulakayala, N.I.; Kumar, K.M.; Rapolu, R.K.; Kandagatla, B.; Rao, P.; Oruganti, S.; Pal, M. Tetrahedron Lett., 2012, 53, 6004.
(i)Begum, T.; Gogoi, A.; Gogoi, P.K.; Bora, U. Tetrahedron Lett., 2015, 56, 95.
(j)Wagh, R.B.; Nagarkar, J.N. Tetrahedron Lett., 2017, 58, 3323.
(b)Mahanta, A.; Adhikari, P.; Bora, U.; Thakur, A.J. Tetrahedron Lett., 2015, 56, 1780.
(c)Gogoi, K.; Dewan, A.; Gogoi, A.; Borah, G.; Bora, U. Heteroatom Chem., 2014, 25, 127.
(d)Gogoi, A.; Bora, U. Tetrahedron Lett., 2013, 54, 1821.
(e)Saikia, E.; Bora, S.J.; Chetia, B. RSC. Adv., 2015, 5, 102723.
(f)Prakash, G.K.S.; Chacko, S.; Panja, C.; Thomas, T.E.; Gurung, L.; Rasul, G.; Mathew, T.; Olah, G.A. Adv. Synth. Catal., 2009, 351, 1567.
(g)Gogoi, A. Bora. U. Synlett, 2012, 23, 1079.
(h)Mulakayala, N.I.; Kumar, K.M.; Rapolu, R.K.; Kandagatla, B.; Rao, P.; Oruganti, S.; Pal, M. Tetrahedron Lett., 2012, 53, 6004.
(i)Begum, T.; Gogoi, A.; Gogoi, P.K.; Bora, U. Tetrahedron Lett., 2015, 56, 95.
(j)Wagh, R.B.; Nagarkar, J.N. Tetrahedron Lett., 2017, 58, 3323.
[13]
Saha, A.; Payra, S.; Dutta, D.; Banerjee, S. ChemPlusChem, 2017, 82, 1129.
[http://dx.doi.org/10.1002/cplu.201700221] [PMID: 31957327]
[http://dx.doi.org/10.1002/cplu.201700221] [PMID: 31957327]
[14]
(a)Gualandi, A.; Savoini, A.; Saporetti, R. Org. Chem. Frontiers, 2018, 5, 1573.
[http://dx.doi.org/10.1039/C8QO00061A]
(b)Silveira-Dorta, G.; Monzón, D.M.; Crisóstomo, F.P.; Martín, T.; Martín, V.S.; Carrillo, R. Chem. Commun., 2015, 51, 7027.
(c)Matsui, K.; Ishigami, T.; Yamaguchi, T.; Yamaguchi, E.; Tada, N.; Miura, T.; Itoh, A. Synlett, 2014, 25, 2613.
[http://dx.doi.org/10.1039/C8QO00061A]
(b)Silveira-Dorta, G.; Monzón, D.M.; Crisóstomo, F.P.; Martín, T.; Martín, V.S.; Carrillo, R. Chem. Commun., 2015, 51, 7027.
(c)Matsui, K.; Ishigami, T.; Yamaguchi, T.; Yamaguchi, E.; Tada, N.; Miura, T.; Itoh, A. Synlett, 2014, 25, 2613.
[15]
(a)Pitre, S.P.; McTiernan, C.D.; Ismaili, H.; Scaiano, J.C. J. Am. Chem. Soc., 2013, 135, 13286.
(b)Toyao, T.; Ueno, N.; Miyahara, K.; Matsui, Y.; Kim, T.H.; Horiuchi, Y.; Ikeda, H.; Matsuoka, M. Chem. Commun. (Camb.), 2015, 51, 16103.
(c)Zhang, M.J.; Li, H.X.; Li, H.Y.; Lang, J.P. Dalton Trans., 2016, 45, 17759.
(d)Yu, X.; Cohen, S.M. Chem. Commun. (Camb.), 2015, 51, 9880.
(e)Luo, J.; Zhang, X.; Zhang, J. ACS Catal., 2015, 5, 2250.
(f)Johnson, J.A.; Luo, J.; Zhang, X.; Chen, Y.S.; Morton, M.D.; Echeverría, E.; Torres, F.E.; Zhang, J. ACS Catal., 2015, 5, 5283.
(g)Xie, H.Y.; Han, L.S.; Huang, S.; Lei, X.; Cheng, Y.; Zhao, W.; Sun, H.; Wen, X.; Xu, Q.L. J. Org. Chem., 2017, 82, 5236.
(h)Tobin, J.M.; McCabe, T.J.D.; Prentice, A.W.; Holzer, S.; Lloyd, G.O.; Paterson, M.J.; Arrighi, V.; Cormack, P.A.G.; Vilela, F. ACS Catal., 2017, 7, 4602.
(i)Wei, P.F.; Qi, M.Z.; Wang, Z.P.; Ding, S.Y.; Yu, W.; Liu, Q.; Wang, L.K.; Wang, H.Z.; An, W.K.; Wang, W. J. Am. Chem. Soc., 2018, 140, 4623.
(b)Toyao, T.; Ueno, N.; Miyahara, K.; Matsui, Y.; Kim, T.H.; Horiuchi, Y.; Ikeda, H.; Matsuoka, M. Chem. Commun. (Camb.), 2015, 51, 16103.
(c)Zhang, M.J.; Li, H.X.; Li, H.Y.; Lang, J.P. Dalton Trans., 2016, 45, 17759.
(d)Yu, X.; Cohen, S.M. Chem. Commun. (Camb.), 2015, 51, 9880.
(e)Luo, J.; Zhang, X.; Zhang, J. ACS Catal., 2015, 5, 2250.
(f)Johnson, J.A.; Luo, J.; Zhang, X.; Chen, Y.S.; Morton, M.D.; Echeverría, E.; Torres, F.E.; Zhang, J. ACS Catal., 2015, 5, 5283.
(g)Xie, H.Y.; Han, L.S.; Huang, S.; Lei, X.; Cheng, Y.; Zhao, W.; Sun, H.; Wen, X.; Xu, Q.L. J. Org. Chem., 2017, 82, 5236.
(h)Tobin, J.M.; McCabe, T.J.D.; Prentice, A.W.; Holzer, S.; Lloyd, G.O.; Paterson, M.J.; Arrighi, V.; Cormack, P.A.G.; Vilela, F. ACS Catal., 2017, 7, 4602.
(i)Wei, P.F.; Qi, M.Z.; Wang, Z.P.; Ding, S.Y.; Yu, W.; Liu, Q.; Wang, L.K.; Wang, H.Z.; An, W.K.; Wang, W. J. Am. Chem. Soc., 2018, 140, 4623.
[16]
(a)Shin, E.J.; Kwon, G.T.; Kim, S.H. Synlett, 2019, 30, 1815.
(b)Shin, E.J.; Kim, H.S.; Joo, S.R.; Shin, U.S.; Kim, S.H. Catal. Lett., 2019, 149, 1560.
(c)Joo, S.R.; Kwon, G.T.; Park, S.Y.; Kim, S.H. Bull. Korean Chem. Soc., 2019, 40, 465.
(d)Shin, E.J.; Joo, S.R.; Kim, S.H. Tetrahedron Lett., 2019, 55, 1509.
(b)Shin, E.J.; Kim, H.S.; Joo, S.R.; Shin, U.S.; Kim, S.H. Catal. Lett., 2019, 149, 1560.
(c)Joo, S.R.; Kwon, G.T.; Park, S.Y.; Kim, S.H. Bull. Korean Chem. Soc., 2019, 40, 465.
(d)Shin, E.J.; Joo, S.R.; Kim, S.H. Tetrahedron Lett., 2019, 55, 1509.
[17]
(a)Molander, G.A.; Cavalcanti, L.N.; Canturk, B.; Pan, P.S.; Kenndy, L.E. J. Org. Chem., 2009, 74, 7364.
[http://dx.doi.org/10.1021/jo901441u]
(b)Gillis, E.P.; Burke, M.D. J. Am. Chem. Soc., 2007, 129, 6716.
[http://dx.doi.org/10.1021/ja0716204]
[http://dx.doi.org/10.1021/jo901441u]
(b)Gillis, E.P.; Burke, M.D. J. Am. Chem. Soc., 2007, 129, 6716.
[http://dx.doi.org/10.1021/ja0716204]
[18]
Gohain, M.; du Plessiss, M.; van Tonder, J.H. Bezuidenhoudt B.C.B. Tetrahedron Lett., 2014, 55, 2082.
[http://dx.doi.org/10.1016/j.tetlet.2014.02.048]
[http://dx.doi.org/10.1016/j.tetlet.2014.02.048]
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