Double bonds are a versatile platform for simultaneously introducing two functional groups, rendering double bond functionalization a widely embraced strategy in organic synthesis1. The pursuit of enantioselective transformations has been predominantly led by transition metal catalysis, although recent interest in organocatalysis has been notable, albeit with limited exploration of group 16 based Lewis base catalysis. Lewis base catalysis involves the sharing of Lewis base (LB) electrons with Lewis acid (LA), yielding a reactive intermediate with enhanced reactivity2. Notably, when the Lewis base is chiral, it can promote the transfer of hyperactive electrophiles in an asymmetric fashion3. On the other hand, the significance of sulfur-containing compounds, including natural products and pharmaceuticals, is well-established4, with SCF3 emerging as a potent group due to its heightened lipophilicity and permeability5. In light of these considerations, the alkyl/arylthio and trifluoromethylthiofunctionalization of alkenes emerged as pressing objectives in organic synthesis. And synthesis of these products using S and Se based Lewis bases is highly warranted. Following a comprehensive literature review, our discussion will pivot towards exploring potential research proposals in this domain.


References:
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2. Matviitsuk, A.; Panger, J. L.; Denmark, S. E. Angew. Chemie Int. Ed. 2020, 59 (45), 19796–19819.
3. Denmark, S. E.; Jaunet, A. J. Am. Chem. Soc. 2013, 135 (17), 6419–6422
4. Denmark, S. E.; Chi, H. M.,. J. Am. Chem. Soc. 2014, 136 (25), 8915–8918.
5. Liu, X.; An, R.; Zhang, X.; Luo, J.; Zhao, X. Angew. Chem. Int. Ed. 2016, 55, 5846–5850