A Traceless Tether Strategy for Achieving Formal Intermolecular Hexadehydro-Diels-Alder Reactions

Merrick Pierson Smela, Thomas R Hoye

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A synthetic strategy formally equivalent to an intermolecular hexadehydro-Diels-Alder (HDDA) reaction is described. Sulfur-based linkers were designed and constructed by joining terminal alkynes or diynes using alkyne thiolate chemistry. The resulting tetraynes and triynes successfully underwent HDDA cyclization and benzyne trapping. Linker removal by reductive desulfurization was uneventful. The strategy was also found suitable for the tetradehydro-Diels-Alder (TDDA) reaction.

Original languageEnglish (US)
Pages (from-to)5502-5505
Number of pages4
JournalOrganic Letters
Volume20
Issue number17
DOIs
StatePublished - Sep 7 2018

Fingerprint

Diels-Alder reactions
Alkynes
Cycloaddition Reaction
alkynes
Diynes
Alnus
Cyclization
Desulfurization
Sulfur
Joining
sulfur
trapping
chemistry
benzyne

PubMed: MeSH publication types

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

Cite this

A Traceless Tether Strategy for Achieving Formal Intermolecular Hexadehydro-Diels-Alder Reactions. / Smela, Merrick Pierson; Hoye, Thomas R.

In: Organic Letters, Vol. 20, No. 17, 07.09.2018, p. 5502-5505.

Research output: Contribution to journalArticle

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