The fluorinated organic molecules are known to have various advantages, such as their ability to enhance metabolic stability, greater lipophilicity and increase bioavailability.1 Due to these widespread application the selective introduction of fluorinated moiety have paid considerable attention in pharmaceutical, agrochemical, and advanced functional material chemistry.2 Among these fluorinated moiety the strong electronegativity and high lipophilicity (Hansch parameter π = 1.44) of trifluoromethylthiol group (–SCF3) further increase the therapeutic potential of bioactive organic compounds.3 Hence, a visible-light-driven organophotocatalyzed multi-component approach has been developed for tandem direct C(sp3)–H activation, alkylation, and followed by trifluoromethyl/aryl/alkylthiolation in one-pot operation. We report a completely metal-free, tandem one-pot three-component approach for the difunctionalization of activated alkenes via the photoinduced radical pathway. This protocol allows two new C(sp3)–C(sp3) and C(sp3)–S bond formation using bench stable, easy to handle trifluoromethyl/aryl/alkylthiolating reagents under mild reaction conditions. The generosity of this reaction has been proven over a library of C(sp3)–H donors, alkenes, trifluoromethyl/aryl/alkyl/thiol derivatives. A wide variety of functional groups are tolerant to our reaction conditions, and the gram-scale reaction using environmentally benign and straightforward conditions shows the synthetic advancement of our developed methodology.

Visible-light-driven organophotocatalyzed one-pot multi-component approach for tandem C(sp3)–H activation, alkylation followed by trifluoromethyl/aryl/alkylthiolation

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27th CRSI National Symposium in Chemistry

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