Ring-closing metathesis of fluoroalkenes toward the synthesis of fluorinated heterocycles containing an oxaza bond

Kirsch, 2013 Uneyama, 2006 O'Hagan, 2008, Chem. Soc. Rev., 37, 308, 10.1039/B711844A See for examples: Osada, 2010, Bioorg. Med. Chem., 18, 605, 10.1016/j.bmc.2009.12.005 Asahina, 2005, J. Med. Chem., 48, 3194, 10.1021/jm0402061 Oishi, 2009, Org. Biomol. Chem., 7, 2872, 10.1039/b907983a Wren, 2010 Couve-Bonnaire, 2007, Org. Biomol. Chem., 5, 1151, 10.1039/b701559c Lin, 1998, Proc. Natl. Acad. Sci. U.S.A., 95, 14020, 10.1073/pnas.95.24.14020 Pierry, 2013, ChemBioChem, 14, 1620, 10.1002/cbic.201300325 2015 2014 Vougioukalakis, 2010, Chem. Rev., 110, 1746, 10.1021/cr9002424 Fustero, 2015, Chem. Rev., 115, 871, 10.1021/cr500182a Salim, 2003, Org. Lett., 5, 3403, 10.1021/ol035065w De Matteis, 2004, Tetrahedron Lett., 45, 959, 10.1016/j.tetlet.2003.11.093 De Matteis, 2007, Eur. J. Org. Chem., 2667, 10.1002/ejoc.200601119 De Matteis, 2006, Eur. J. Org. Chem., 1166, 10.1002/ejoc.200500826 De Matteis, 2008, Synlett, 351 Cogswell, 2015, Org. Biomol. Chem., 13, 717, 10.1039/C4OB01547A Cogswell, 2016, Org. Biomol. Chem., 14, 183, 10.1039/C5OB02155C Li, 2016, Tetrahedron, 72, 4845, 10.1016/j.tet.2016.06.054 Marhold, 2004, Tetrahedron Lett., 45, 57, 10.1016/j.tetlet.2003.10.127 Marhold, 2014, J. Org. Chem., 5777 Schneider, 2013, Angew. Chem., Int. Ed., 12, 3246, 10.1002/anie.201209446 Rousée, 2016, Org. Biomol. Chem., 14, 353, 10.1039/C5OB02213D Rousée, 2016, Org. Lett., 18, 540, 10.1021/acs.orglett.5b03571 Guerin, 2014, ACS Catal., 4, 2374, 10.1021/cs500559p Guerin, 2016, Org. Lett., 18, 3606, 10.1021/acs.orglett.6b01631 Kirkland, 1998, J. Org. Chem., 63, 9904, 10.1021/jo981678o Rölle, 2002, Chem. Commun., 1070, 10.1039/b201865a Gatti, 2010, J. Am. Chem. Soc., 132, 15179, 10.1021/ja108253f For the use of fluorinated aromatic hydrocarbons (FAH) as efficient solvent in metathesis reaction, see: Grandbois, 2008, Chem. Eur. J., 14, 9323, 10.1002/chem.200801033 Samojlowicz, 2008, Chem. Commun., 6282, 10.1039/b816567j Samojlowicz, 2011, Chem. Eur. J., 17, 12981, 10.1002/chem.201100160 Samojlowicz, 2011, Adv. Synth. Catal., 353, 1993, 10.1002/adsc.201100053 Moss, 2012 Urch, 2015 Desai, 1993, Tetrahedron Lett., 34, 961, 10.1016/S0040-4039(00)77465-X Yang, 2003, Synlett, 7, 1043 Lemonnier, 2009, J. Org. Chem., 74, 4124, 10.1021/jo900422m The use of Grubbs 1 catalyst in CH2Cl2 at 45 °C in various concentrations (see ref [18]) led only to the recovery of starting material. Other experimental conditions (Mo- and Ru-based precatalysts (Schrock catalysts, Grubbs I, Grubbs II, and Hoveyda–Grubbs II), solvent (CH2Cl2 or toluene), concentration (from 0.006 to 0.2 M), temperature (from 45 to 110 °C [under reflux, microwave irradiation or in sealed tubes]), catalyst loading (from 5 to 20%)) were tried without success leading only to the recovery of starting material or degradation. Liu, 2008, Synthesis, 15, 2432 Zemmouri, 2011, J. Org. Chem., 76, 7691, 10.1021/jo200798h