New methodologies for the preparation of (pentafluorosulfanyl)benzenes

Organic compounds with pentafluorosulfanyl (SF5) groups display a unique set of physicochemical properties. This includes extreme kinetic and hydrolytic stability, very strong electron acceptor capability, and high lipophilicity with high SF5 electronegativity. A very high dipole moment can be achieved by the introduction of SF5 group without increasing molecular polarity. These properties make the pentafluorosulfanyl group an increasingly interesting structural motif for the design of bioactive compounds, including agrochemicals and pharmaceuticals as well as functional materials such as polymers or liquid crystals. However, access to SF5-containing compounds is very limited and their chemistry remains largely unexplored.

In this project we are developing new methodologies towards substituted (pentafluorosulfanyl)benzenes (Organic Letters 13: 1466-1469, 2011; Journal of Organic Chemistry 76: 4781-4786, 2011; Tetrahedron Letters 52: 4392-4394, 2011; Journal of Fluorine Chemistry 143: 130-134, 2012; European Journal of Organic Synthesis 2123-2126, 2012; Beilstein Journal of Organic Chemistry 1185-1190, 2012; Beilstein Journal of Organic Chemistry 9: 411-416, 2013; Synlett 855-859, 2013; Journal of Organic Chemistry 79: 8906-8911, 2014; Environmental Science and Pollution Research 21: 753-758, 2014; Journal of Fluorine Chemistry 157: 79-83, 2014; Beilstein Journal of Organic Chemistry 11: 1494-1502, 2015; Chemical Communications 52: 7237-7240, 2016; Beilstein Journal of Organic Chemistry 12: 192–197, 2016; Beilstein Journal of Organic Chemistry 12: 110–116, 2016).