Carbon-sulfur bond (C-S) formations have gained increasing attention in organic synthesis, due to
inevitable presence of organosulfur compounds in many synthetic drugs and bioactive natural
product.1 In addition, aryl sulfides are vital building blocks in general organic synthesis as well as in
the pharmaceutical industry and in material science application.2 On the other hand, fluorine or
fluorine-containing moieties has become an important motifs in drug discovery, which offers
enhanced bioavailability and high activity compare to non-fluorinated analogs.3 Among the fluorine
containing groups, the trifluoromethylthio group (-SCF3) has attracted increasing interest due to its
high lipophilicity property (πR = 1.44), which can greatly increase the transmembrane permeability of
drug candidates.4 Although number of approaches have been documented, functionalizations of arenes
and unsaturated compound with electrophilic thiolating reagent have gained notable interest in the
recent decades. In this context, our group developed number of arylthiolation and
trifluoromethylathiolation strategies using N-S reagents.5 To further expand the utilizity of N-S
reagents, trifluoromethylthiolative and arylthiolative functionalization of arenes and alkenes have
been developed employing either transition metal or metal free conditions.6 The details will be
discussed in the presentation.
References:
[1] Clayden, J.; MacLellan, P. Beilstein J. Org. Chem. 2011, 7, 582.
[2] a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. b) Sun, Z. Y.; Botros, E.; Su, A. D.; Kim, Y.; Wang, E.;
Baturay, N. Z.; Kwon, C. H. J. Med. Chem. 2000, 43, 4160.
[3] a) Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525. b) Manteau, B.; Pezenok, S.; Vors, J. P.;
Leroux, F. R. J. Flourine Chem. 2010, 131, 140.
[4] Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214.
[5] a) Saravanan, P.; Anbarasan, P. Org. Lett. 2014, 16, 848. b) Chaitanya, M.; Anbarasan, P. Org. Lett. 2018,
20, 3362. c) Saravanan, P.; Anbarasan, P. Chem. Commun. 2019, 55, 4639.
[6] Kesavan, A.; Chaitanya, M.; Anbarasan, P. Eur. J. Org. Chem. 2018, 25, 3276.