Transition Metal-free Trifluoroethoxylation of Diaryliodonium Salts and Fluoro Alcohols

Author(s): Jian Li* , Zhengbing Wang , Xuechen Lu , Jing Lin , Li Liu , Yue Zhao .

Journal Name: Letters in Organic Chemistry

Volume 16 , Issue 6 , 2019

Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

A method for the synthesis of aryl trifluoroethyl ethers from fluoroalcohols and diaryliodonium salts in the presence of NaH and warm 1,2-dichloroethane has been developed. This transition metal free reaction is mild and facile. Various functional group including electron-withdrawing and electron-donating substrates in the diaryliodonium salts were tolerated in this transformation to afford the products in moderate to high yields.

Keywords: Diaryliodonium salts, transition metal free reactions, trifluoroethoxylation, organic compound, DMSO, HMPA.

[1]
Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology; Wiley: Hoboken, 2009.
[2]
Khotavivattana, T.; Verhoog, S.; Tredwell, M.; Pfeifer, L.; Calderwood, S.; Wheelhouse, K.; Collier, L.T.; Gouverneur, V. Angew. Chem. Int. Ed., 2015, 54, 9991-9995.
[3]
Xu, X-H.; Matsuzaki, K.; Shibata, N. Chem. Rev., 2015, 115, 731-764.
[4]
Sanford, M.S.; Scott, P.J. ACS Cent. Sci., 2016, 2, 128-130.
[5]
Bégué, J-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley: Hoboken, 2008.
[6]
Legros, J.; Dehli, J.R.; Bolm, C. Adv. Synth. Catal., 2005, 347, 19-31.
[7]
Camps, F.; Coll, J.; Messeguer, A.; Pericàs, M.A. Synthesis, 1980, 9, 727-728.
[8]
Kamal, A.; Pratap, T.B.; Ramana, K.V.; Ramana, A.V.; Babu, A.H. Tetrahedron Lett., 2002, 43, 7353-7355.
[9]
Keegstra, M.A.; Brandsma, L. Recl. Trav. Chim. Pays Bas, 1991, 110, 299-300.
[10]
Vuluga, D.; Legros, J.; Crousse, B.; Bonnet-Delpon, D. Eur. J. Org. Chem., 2009, 3513-3518.
[11]
Rangarajan, T.M.; Singh, R.; Brahma, R.; Devi, K.; Singh, R.P.; Prasad, A.K. Chem. Eur. J., 2014, 20, 14218-14225.
[12]
Huang, R.; Huang, Y.; Lin, X.; Rong, M.; Weng, Z. Angew. Chem. Int. Ed., 2015, 54, 5736-5739.
[13]
Yang, L.; Li, S.; Cai, L.; Ding, Y.; Fu, L.; Cai, Z.; Ji, H.; Li, G. Org. Lett., 2017, 19, 2746-2749.
[14]
Bielawski, M.; Olofsson, B. Chem. Commun., 2007, 2521-2523.
[15]
Storr, T.E.; Greaney, M.F. Org. Lett., 2013, 15, 1410-1413.
[16]
Suero, M.G.; Bayle, E.D.; Collins, B.S.L.; Gaunt, M.J. J. Am. Chem. Soc., 2013, 135, 5332-5335.
[17]
Holt, D.; Gaunt, M.J. Angew. Chem. Int. Ed., 2015, 54, 7857-7861.
[18]
Chan, L.; McNally, A.; Toh, Q.Y.; Mendoza, A.; Gaunt, M.J. Chem. Sci., 2015, 6, 1277-1281.
[19]
Wagner, A.M.; Sanford, M.S. J. Org. Chem., 2014, 79, 2263-2267.
[20]
Tolnai, G.L.; Nilsson, U.J.; Olofsson, B. Angew. Chem. Int. Ed., 2016, 55, 11226-11230.
[21]
Wang, M.; Wei, J.; Fan, Q.; Jiang, X. Chem. Commun., 2017, 53, 2918-2921.
[22]
Modha, S.G.; Greaney, M.F. J. Am. Chem. Soc., 2015, 137, 1416-1419.
[23]
Tinnis, F.; Stridfeldt, E.; Lundberg, H.; Adolfsson, H.; Olofsson, B. Org. Lett., 2015, 17, 2688-2691.
[24]
Sheng, J.; Su, X.; Cao, C.; Chen, C. Org. Chem. Front., 2016, 3, 501-504.
[25]
Sheng, J.; Wang, Y.; Su, X.; He, R.; Chen, C. Angew. Chem. Int. Ed., 2017, 129, 4902-4906.
[26]
Li, J.; Wang, H.; Sun, J.; Yang, Y.; Liu, L. Org. Biomol. Chem., 2014, 12, 7904-7908.
[27]
Liu, L.; Qiang, J.; Bai, S.; Sung, H.; Miao, C.; Li, J. Adv. Synth. Catal., 2017, 359, 1283-1289.
[28]
Jalalian, N.; Ishikawa, E.E.; Silva, Jr , L.F.; Olofsson, B. Org. Lett., 2011, 13, 1552-1555.
[29]
Lindstedt, E.; Ghoshand, R.; Olofsson, B. Org. Lett., 2013, 15, 6070-6073.
[30]
Lindstedt, E.; Stridfeldt, E.; Olofsson, B. Org. Lett., 2016, 18, 4234-4237.
[31]
Sundalam, S.K.; Stuart, D.R. J. Org. Chem., 2015, 80, 6456-6466.
[32]
(a)Low, C.M.R. Sci. Syn., 2007, 31a, 547-625.
(b)Ricci, P.; Kramer, K.; Larrosa, I. J. Am. Chem. Soc., 2014, 136, 18082-18086.
(c)Guo, Y.; Li, Y-D.; Chen, C.; Zhao, J-H.; Liu, H-W.; Liao, D-H.; Ji, Y-F. Res. Chem. Intermediat., 2016, 42, 2525-2537.
(d)Zhang, K.; Xu, X-H.; Qing, F-L. J. Fluor. Chem., 2017, 196, 24-31.
(e)Liu, L.; Bai, S.; Zhu, Y.; Li, J. Synthesizing method of trifluoroethoxyl aryl ether derivative. CN 107200681, September 26 2017.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 16
ISSUE: 6
Year: 2019
Page: [485 - 490]
Pages: 6
DOI: 10.2174/1570178615666181108111232
Price: $58

Article Metrics

PDF: 24
HTML: 3