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

Qile Wang, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish (US)
Pages (from-to)5448-5451
Number of pages4
JournalOrganic Letters
Volume23
Issue number14
DOIs
StatePublished - Jul 16 2021

Bibliographical note

Funding 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).

Publisher Copyright:
© 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.

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