Ni-Catalyzed Reductive Cross-Coupling Between Aryl Halides And Allyl Halides

Isoprenylated arenes are found in the structure of many natural products, which demonstrate biological and pharmacological activities. The preparation of prenylated arenes, involves the introduction of prenyl or related 3,3-disubstituted allyl groups onto functionalized aromatic systems, In this context, the exclusive control of regioselectivity remains a great challenge. Nickel catalysts is relatively cheap, it has been widely used in organic synthesis as a catalyst for the formation of carbon-carbon and carbon-heteroatom bonds, nickel catalyzed direct reductive cross-coupling reaction to construct C-C bonds has recently received significant attention. In this work, we report a nickel-catalyzed direct reductive cross-coupling reaction of aryl halides with readily accessible polysubstituted allyl halides for the rapid assembly of a wide range of allylation arenes under mild conditions. The main content is summarized below:1. We introduced the research progress of metal-catalyzed allylic substitution reactions and a detailed description of the Palladium-catalyzed allylation; We also made a brief introdction of other metal-catalyzed such as Molybdenum, Iridium, Copper, Nickel, Rhodium and Ruthenium. Then we summarized the allyl electrophiles, including allyl ether, allyl ester, allyl sulfone, allyl halide, allyl alcohol and allyl amine compounds in the Palladium-catalyzed allylation.2. We introduced a nickel-catalyzed direct reductive cross-coupling reaction of aryl halides with readily accessible polysubstituted allyl halides for the rapid assembly of a wide range of allylation arenes under mild conditions. Notable features of this transformation include the mild reaction conditions, the readily available starting materials, and a broad substrate scope. At the same time, we attempted to exploit the full potential of our nickel-catalyzed reductive cross-coupling by synthesizing the diprenyl derivative of curcumin (PCRM), and it possesses excellent anticarcinogenic and antiinflammatory properties.