SYNTHESIS AND ELECTRONIC PROPERTIES OF 3-ARYL 10H-PHENOTHIAZINES
Keywords:
Cross-coupling – DFT calculations – Heterocycles – Substituent Effects – UV/Vis SpectroscopyAbstract
3-Bromo 10H-phenothiazines, even the 10H-unsubstituted derivative, can be efficiently coupled with several boronic acids to give 3-aryl 10H-phenothiazines with good to excellent yields. Selected electronic properties (UV/Vis spectroscopy, cyclic voltammetry, DFT calculations) are discussed and correlations of the Hammett-Taft substituent parameters are established for rationalizing the transmission of the remote electronic substituent effects.
References
A. Suzuki, Acc. Chem. Res. 1982, 15, 178-184. b) T. Watanabe, N. Miyaura, A. Suzuki, Synlett 1992, 207-210. c) T. Oh-e, N. Miyaura, A. Suzuki, J. Org. Chem. 1993, 58, 2201-2208. d) A. Suzuki, Pure Appl. Chem. 1994, 66, 213-222. e) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2383. f) A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168. g) A.D. Schlüter, J. Polym. Sci.: Part A: Polym. Chem. 2001, 39, 1533-1556. S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633-9695.
A. Bende, I. Grosu, I. Turcu, J. Phys. Chem. A 2010, 114, 12479-12489. b) E. Gal, C. Cristea, L. Silaghi-Dumitrescu, T. Lovasz, A. Csampai, Tetrahedron 2010, 66, 9938-9944. c) L. Gaina, C. Cristea, C. Moldovan, D. Porumb, E. Surducan, C. Deleanu, A. Mahamoud, J. Barbe, I. A. Silberg, Int. J. Mol. Sci. 2007, 8, 70-80. d) I. A. Silberg, G. Cormos, D. C. Oniciu In Adv. Heterocycl. Chem., A. R. Katritzky, ed., 2006, 90, 205-237. e) D. Dicu, L. Muresan, I. C. Popescu, C. Cristea, I. A. Silberg, P. Brouant, Electrochim. Acta 2000, 45, 3951-3957. f) I. A. Silberg, C. Cristea, Heterocycl. Commun. 1996, 2, 117-124.
K. Okada, T. Imakura, M. Oda, H. Murai, M. Baumgarten, J. Am. Chem. Soc. 1996, 118, 3047-3048.
R. Duesing, G. Tapolski, T.J. Meyer, J. Am. Chem. Soc. 1990, 112, 5378-5379.
W.E. Jones, P. Chen, T.J. Meyer, J. Am. Chem. Soc. 1992, 114, 387-388.
J. Daub, R. Engl, J. Kurzawa, S.E. Miller, S. Schneider, A. Stockmann, M.R. Wasielewski, J. Phys. Chem. A 2001, 105, 5655-5665.
M. Sailer, A.W. Franz, T.J.J. Müller, Chem. Eur. J. 2008, 14, 2602-2614.
K. Memminger, T. Oeser, T.J.J. Müller, Org. Lett. 2008, 10, 2797-2800.
G. Zhou, N. Pschirer, J.C. Schöneboom, F. Eickemeyer, M. Baumgarten, K. Müllen, Chem. Mater. 2008, 20, 1808-1815.
M. Hauck, M. Stolte, J. Schönhaber, H.-G. Kuball, T.J.J. Müller, Chem. Eur. J. 2011, 17, 9984-9998.
M. Hauck, J. Schönhaber, A.J. Zucchero, K.I. Hardcastle, T.J.J. Müller, U.H. F. Bunz, J. Org. Chem. 2007, 72, 6714-6725.
N. Bucci, T.J.J. Müller, Tetrahedron Lett. 2006, 47, 8329-8332.
N. Bucci, T.J.J. Müller, Tetrahedron Lett. 2006, 47, 8323-8327.
S. Bay, T. Villnow, G. Ryseck, V. Rai-Constapel, P. Gilch, T.J.J. Müller, ChemPlusChem 2013, 78, 137-141.
S. Bay, G. Makhloufi, C. Janiak, T.J.J. Müller, Beilstein J. Org. Chem. 2014, 10, 1006-1016.
S. Bay, T.J.J. Müller, Z. Naturforsch. 2014, 69b, 541-553.
T.J.J. Müller, A. W. Franz, C. S. Barkschat (née Krämer), M. Sailer, K. Meerholz, D. Müller, A. Colsmann, U. Lemmer, Macromol. Symp. 2010, 287, 1-7.
Z. Zhou, A. W. Franz, M. Hartmann, A. Seifert, T.J.J. Müller, W. R. Thiel, Chem. Mater. 2008, 20, 4986-4992.
T. Meyer, D. Ogermann, A. Pankrath, K. Kleinermanns, T.J.J. Müller, J. Org. Chem. 2012, 77, 3704-3715.
H. Tian, X. Yang, R. Chen, Y. Pan, L. Li, A. Hagfeldt, L. Sun, Chem. Commun. 2007, 3741-3743.
S. S. Park, Y. S. Won, Y. C. Choi, J. H. Kim, Energy Fuels 2009, 23, 3732-3736.
C. Lambert, V. Kriegisch, Langmuir 2006, 22, 8807-8812.
C. S. Barkschat, S. Stoycheva, M. Himmelhaus, T.J.J. Müller, Chem. Mater. 2010, 22, 52-63.
A. W. Franz, S. Stoycheva, M. Himmelhaus, T.J.J. Müller, Beilstein J. Org. Chem. 2010, 6, No 72. doi:10.3762/bjoc.6.72.
J. Rechmann, A. Sarfraz, A. C. Götzinger, E. Dirksen, T.J.J. Müller, A. Erbe, Langmuir 2015, 31, 7306-7316.
For synthesis of phenothiazinyl boronic acid derivatives, see e. g. a) C. S. Krämer, T.J. Zimmermann, M. Sailer, T.J.J. Müller, Synthesis 2002, 1163-1170. b) A.W. Franz, T.J.J. Müller, Synthesis 2008, 1121-1125.
For representative phenothiazine functionalization with phenothiazinyl boronates, see e. g. a) C.S. Krämer, K. Zeitler, T.J.J. Müller, Tetrahedron Lett. 2001, 42, 8619-8624. b) M. Sailer, F. Rominger, T.J.J. Müller, J. Organomet. Chem. 2006, 691, 299-308. c) M. Sailer, M. Nonnenmacher, T. Oeser, T.J.J. Müller, Eur. J. Org. Chem. 2006, 423-435. d) M. Hauck, R. Turdean, K. Memminger, J. Schönhaber, F. Rominger, T.J.J. Müller, J. Org. Chem. 2010, 75, 8591-8603.
J. Cymerman-Craig, W.P. Rogers, G.P. Warwick, Austr. J. Chem. 1955, 8, 252-257.
S. Ebdrup, Austr. J. Chem.Soc., Perkin Trans. 1 1998, 1147-1150.
Y.S. Kang, P. Baglioni, H.J.D. McManus, L. Kevan, J. Phys. Chem. 1991, 95, 7944-7947.
N.S. Angerman, S.S. Danyluk, Org. Magn. Res. 1972, 4, 895-906.
M.A. Palafox, M. Gil, J.L. Nunez, G. Tardajos, Int. J. Quant. Chem. 2002, 89, 147-171.
E. Wagner, S. Filipek, M.K. Kalinowski, Monatsh. Chem. 1988, 119, 929-932.
P. Zanello, in: Ferrocenes (Eds.: A. Togni, T. Hayashi), VCH, Weinheim, New York, Basel, Cambridge, Tokyo, 1995, pp 317-430.
T.J. Kemp, P. Moore, G.R. Quick, J. Chem. Soc. Perkin Trans. II 1980, 291-295.
W.T. Dixon, D. Murphy, J. Chem. Soc. Perkin Trans. II 1976, 1823-1828.
J.A. Elix, K.L. Gaul, D.C.R. Hockless, J.H. Wardlaw, Aust. J. Chem. 1995, 48, 1049-1053.
J.E. Bloor, B.R. Gilson, R.J. Haas, C.L. Zirkle, J. Med. Chem. 1970, 13, 922-925.
M. Jonsson, D.D.M. Wayner, J. Lusztyk, J. Phys. Chem. 1996, 100, 17539-17543.
N.R. Armstrong, R.K. Quinn, N. E. Vanderborgh, Anal. Chem. 1974, 46, 1759-1764.
C. Hansch , A. Leo, R.W. Taft, Chem. Rev. 1991, 91, 165-195.
Application of B3LYP 6–31 G* density functionals as implemented in SPARTAN '08 V 1.2.0, Wavefunction Inc., Irvine, 2008.
H.G.O. Becker, W. Berger, G. Domschke, E. Fanghänel, J. Faust, M. Fischer, F. Gentz, K. Gewald, R. Gluch, R. Mayer, K. Müller, D. Pavel, H. Schmidt, K. Schollberg, K. Schwetlick, E. Seiler, G. Zeppenfeld, Organikum, 20th ed., Johann Ambrosius Barth, Heidelberg, Leipzig, 1996.
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