Study On Alkene Arylalkylation Enabled By Merging Re-catalysis With Hypervalent Iodine(Ⅲ) Reagents Via Decarboxylation

The element of rhenium lies on the intersection of the early and late transition metals inthe periodoic table, which renders rhenium a potential candidate possessing the benefits ofboth early and late transition metals. Relative to the late transition metal rhodium, ruthenium,palladium, etc., the current internationally research for rhenium metal-catalyzed reactions oforganic chemistry is relatively rare, which is in the infancy stage. It’s necessary to developnew catalytic cycles for rhenium species through the novel strategies such as transmetalationand redox chemistry.As reported in the literature and based on our previous work, rhenium plays a specialrole in building the C-C bond and C-X bond (X=O, N, Si, B, etc.). In this paper, we use thethe simple carboxylic acid to prepare the hypervalent iodine (III) reagent, and then we firstaccomplish the “Alkene arylalkylation Enabled by Merging Re-catalysis with HypervalentIodine(III) Reagents via Decarboxylation”. Finally we efficientlly and selectively build aseries of3,4-dihydroquinolinone and3,3-disubstituted oxindole derivatives, which havehighly synthetic value and can be widely found in natural products, pharmaceutical chemicalsand agrochemicals. It is worth mentioning that our reaction systerm can tolerant many kindsof functional groups. Thus, it allows for a rapid access to a variety of3,4-dihydroquinolinoneand3,3-disubstituted oxindoles.This paper has the following work:1. Internal alkene arylalkylation enabled by merging rhenium-catalysis with hypervalentiodine(III) reagents to give twelve3,4-dihydroquinolinone compouds.2.Terminal alkene arylalkylation enabled by merging rhenium-catalysis with hypervalentiodine(III) reagents to give twenty-three3,3-disubstituted oxindole compouds.3.Synthsis of substrates: N-methyl-N-phenylmethacrylamides、 N-methyl-N-phenylcinnamamides and hypervalent iodine(III) reagentsThis paper has the following innovations:1. First example of alkene arylalkylation enabled by merging rhenium-catalysis with hypervalent iodine(III) reagents.2. Efficientlly and selectively building3,4-dihydroquinolinone and3,3-disubstitutedoxindole derivatives respectively.3. The mechanism is proved to be a tandem process including decarboxylation, radicaladdition and annulation.