Cyclization strategies to polyenes using Pd(II)-catalyzed couplings of pinacol vinylboronates

Robert G. Iafe, Daniel G. Chan, Jonathan L. Kuo, Byron A. Boon, Darius J. Faizi, Tomomi Saga, Jonathan W. Turner, Craig A. Merlic

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

As a complement to Pd(0)-catalyzed cyclizations, seven Pd(II)-catalyzed cyclization strategies are reported. α,ω-Diynes are selectively hydroborated to bis(boronate esters), which cyclize under Pd(II)-catalysis producing a diverse array of small, medium, and macrocyclic polyenes with controlled E,E, Z,Z, or E,Z stereochemistry. Various functional groups are tolerated including aryl bromides, and applications are illustrated.

Original languageEnglish (US)
Pages (from-to)4282-4285
Number of pages4
JournalOrganic Letters
Volume14
Issue number16
DOIs
StatePublished - Aug 17 2012

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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