A broad‐spectrum synthesis of Tetravinylethylenes

Research output: Contribution to journalArticlepeer-review

Authors

  • Kelsey Horvath
  • Christopher Newton
  • Kim Roper
  • Jas S Ward
  • Michael Sherburn

Colleges, School and Institutes

Abstract

The first general synthesis of compounds of the tetravinylethylene (TVE) family is reported. Ramirez‐type dibromo‐olefination of readily accessible penta‐1,4‐dien‐3‐ones generates 3,3‐dibromo[3]dendralenes, which undergo twofold Negishi, Suzuki‐Miyaura or Mizoroki‐Heck reactions with a wide variety of olefinic coupling partners. This route delivers a broad range of unsymmetrically–substituted tetravinylethylenes with up to three different alkenyl substituents attached to the central C=C bond. The extensive scope of the approach is demonstrated by the preparation of the first higher order oligo‐alkenic through‐conjugated/cross‐conjugated hybrid compounds. An unsymmetrically‐substituted TVE is shown to undergo a domino electrocyclization‐cycloaddition with high site‐selectivity and diastereoselectivity, thereby demonstrating the substantial synthetic potential of substituted TVEs for controlled, rapid structural complexity generation.

Details

Original languageEnglish
Pages (from-to)4072-4076
Number of pages5
JournalChemistry: A European Journal
Volume25
Issue number16
Early online date6 Feb 2019
Publication statusPublished - 15 Mar 2019

Keywords

  • cross-coupling, cycloaddition, electrocyclic reactions, hydrocarbons, polyenes