A novel visible-light-induced trifluoromethylarylation/1,4-aryl shift/desulfonylation cascade reaction using CF3SO2Cl as CF3 source was described. The protocol provides an efficient approach for the synthesis of α-aryl-β-trifluoromethyl amides and/or CF3-containing oxindoles as well as the isoquinolinediones under benign conditions.

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A phosphine‐catalyzed [4 + 2] annulation of α‐substituted allenoate with exocyclic alkene moiety of oxindoles or indan‐1,3‐diones has been developed. Thus, under the catalysis of PPh3 (20 mol%), a series of spirooxindole‐ or spiroindan‐1,3‐dione‐cyclohexenes have been obtained in moderate to excellent yields and regioselectivity from the annulations of α‐methyl allenoates with 3‐methyleneoxindoles or 2‐methyleneindan‐1,3‐diones. This method offers an easy access to structurally novel spirocyclohexenes.

An amine‐catalyzed reaction between Morita–Baylis–Hillman (MBH) acetates and isatins to provide facile access to structurally interesting 3‐hydroxyoxindoles in moderate to good yields with diastereomeric ratios of 1:1 has been developed. A wide variety of isatin derivatives were tolerated under the conditions of this tandem reaction. Notably, the inert homoallylic methyl group of MBH acetate 1 was directly involved in the bond formation step, which was followed by a [4+2] annulation under mild conditions to lead to the desired products.

Difunctionalization of Alkenes via the Visible-Light-Induced Trifluoromethylarylation/1,4-Aryl Shift/Desulfonylation Cascade Reactions. -,-Unsaturated imide alkenes are found to undergo a visible light induced trifluoromethylarylation/ 1,4-aryl shift/desulfonylation cascade to yield oxindoles. N-Arylated substrates give open chain amides (V), whereas imide alkenes (VI) having an aroyl substituent give isoquinolinediones (VII) as products. -(ZHENG, L.; YANG, C.; XU, Z.; GAO, F.; XIA*, W.; J. Org. Chem. 80 (2015) 11, 5730-5736, http://dx.doi.org/10.1021/acs.joc.5b00677 ; State Key Lab. Urban Water Resour. Environ., Harbin Inst. Technol., Harbin 150080, Peop. Rep. China; Eng.) -Mais 41-063