"Kobayashi benzynes" as hexadehydro-diels-alder diynophiles

Sahil Arora, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

We report here elaboration of a cascade strategy for naphthyne formation using Kobayashi benzynes as diynophiles in a subsequent in situ hexadehydro-Diels-Alder reaction. Density functional theory computations suggest that the strained benzynes act as "super-diynophiles"in this transformation. The reaction requires only mildly basic and ambient temperature conditions and allows for rapid construction of various naphthalenic products. The trapping efficiencies of several arynophiles were determined using the benzyne to naphthyne cyclization as an internal clock reaction.

Original languageEnglish (US)
Pages (from-to)3349-3353
Number of pages5
JournalOrganic Letters
Volume23
Issue number9
DOIs
StatePublished - May 7 2021

Bibliographical note

Funding Information:
This research was supported through the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097). Some of the NMR spectral data were acquired with instrumentation acquired with funding through a NIH Shared Instrumentation Grant (S10OD011952). Mass spectrometry was done in the Analytical Biochemistry Shared Resource laboratory in the University of Minnesota, Masonic Cancer Center, which was partially funded by a Cancer Center Support Grant (CA-77598). DFT calculations were done with software and hardware resources provided through the Minnesota Supercomputer Institute.

Funding Information:
This research was supported through the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097). Some of the NMR spectral data were acquired with instrumentation acquired with funding through a NIH Shared Instrumentat i on Grant (S10OD011952). Mass spectrometry was done in the Analytical Biochemistry Shared Resource laboratory in the University of Minnesota, Masonic Cancer Center, which was partially funded by a Cancer Center Support Grant (CA-77598). DFT calculations were done with software and hardware resources provided through the Minnesota Supercomputer Institute.

Publisher Copyright:
© 2021 American Chemical Society.

PubMed: MeSH publication types

  • Journal Article
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

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