10.1002/adsc.201800568
Advanced Synthesis & Catalysis
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Scheme 5. A plausible mechanism for the formation of 3.
In summary, we have developed a novel visible-light-
induced trifluoromethylation of isonitrile-substituted indole
derivatives, giving a variety of 1-(trifluoromethyl)-4,9-dihydro-
3H-pyrido[3,4-b]indole derivatives in moderate to good yields.
This strategy provided a direct process for the construction of a
single C-CF3 bond. The further transformations to β-carboline
derivatives and a CF3-containing harmacine derivative exhibited
the potential synthetic and biological utilities of this method.
Interestingly, the biological activity study also demonstrated that
the obtained CF3-containing product 4d might possess a better
therapeutic effect of treating diabetes. Further investigations on
the application of this methodology to synthesize more interesting
and biologically active compounds are underway in our laboratory.
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Experimental Section
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General Procedure for Synthesis of 3
Isocyanid (0.2 mmol, 1.0 equiv.), Togni’s II reagent (0.3 mmol,
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Detailed descriptions of experimental procedures and their
spectroscopic data as well as the crystal structures are presented in
the Supporting Information. CCDC 1541586 (4a) contains the
supplementary crystallographic data for this paper. These data can
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We are grateful for financial support from the National Basic
Research Program of China [(973)-2015CB856603], the
Strategic Priority Research Program of the Chinese Academy of
Sciences (Grant No. XDB20000000) and sioczz201808, and the
National Natural Science Foundation of China (Nos. 20472096,
21372241, 21572052, 20672127, 21421091, 21372250, 21121062,
21302203, 20732008, 21772037 and 21772226).
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