The first Fe-catalyzed three-component radical trifluoromethyl-alkenylation of alkenes with 2-amino-1,4-naphthoquinones and CF3SO2Na is reported. The developed reaction enables the highly regioselective preparation of a variety of valuable CF3-substituted 1,4-naphthoquinones in acceptable yields. In the light of the catalytic system, alkynes smoothly afford the corresponding three- or four-component trifluoromethyl-alkenylation products. This protocol features use of easily available and inexpensive reagents, broad substrate scope, and simple reaction conditions.

Herein, a simple and efficient strategy that involves dual 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)/iron-catalyzed alkene perfluoroalkylvinylation by using perfluoroalkyl iodides and 2-aminonaphthalene-1,4-diones as coupling partners is demonstrated. In terms of the developed catalytic system, various styrenes and aliphatic alkenes are well-tolerated, leading to the accurate preparation of perfluoroalkyl-containing 2-aminonaphthalene-1,4-diones in excellent regioselectiv-ity. Moreover, the protocol can be readily applied in latestage modifications of natural products and pharmaceuticals. The title reactions are featured by easily accessible and inexpensive catalysts and substrates, broad substrate applicability, and mild reaction conditions. Mechanistic investigations reveal a tandem CÀ I cleavable alkylation and CÀ C vinylation enabled by cooperative DBU/iron catalysis.

This article presents simple and efficient 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted Heck-type alkene perfluoroalkylation under visible light irradiation. With DBU as both a halogen bond acceptor and a base, these transformations can smoothly proceed via a radical process in the absence of an additional photocatalyst. The developed protocol employs alkenes and perfluoroalkyl iodides as readily available substrates and ethyl acetate as a green solvent, affording various perfluoroalkylated alkenes in satisfactory yields under mild conditions.