Cu(I)-Catalyzed 1,2-Alkynyl-propargylation and -benzylation of Benzyne Derivatives

• DOI: 10.1021/acs.orglett.1c01788
• Publication Date: 2021-06-28T14:52:44Z
• Authors: Qile Wang; Thomas R. Hoye
• Keywords: Diynes; Cycloaddition Reaction; Molecular Structure; Pargyline; Benzene Derivatives; 01 natural sciences; Catalysis; Copper; 0104 chemical sciences

We report here a three-component, Cu(I)-catalyzed hexadehydro-Diels-Alder (HDDA) benzyne 1,2-difunctionalization reaction. This protocol allowed the introduction of two different carbon-based substituents onto the in situ-generated benzyne. These substituents were terminal monoynes or diynes partnered with propargylic, benzylic, or allylic chlorides. An example of a sequential HDDA reaction is demonstrated using the product of a 1,3-diyne and a propargylic halide, itself a newly created HDDA precursor.