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.
Bibliographical noteFunding Information:
This research was supported by the National Science Foundation (CHE-1665389) and the National Institute of General Medical Sciences of the National Institutes of Health (NIH) (R35 GM127097). Some of the NMR spectral data were acquired with instrumentation acquired with funding through an NIH Shared Instrumentation Grant (S10OD011952). Mass spectrometry was performed in the Analytical Biochemistry Shared Resource laboratory of the University of Minnesota, Masonic Cancer Center, which was partially funded by a Cancer Center Support Grant (CA-77598).
© 2021 American Chemical Society.
PubMed: MeSH publication types
- Journal Article
- Research Support, N.I.H., Extramural
- Research Support, U.S. Gov't, Non-P.H.S.