Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles: Novel Umpolung Reactivity

Phillip J. Unsworth, Lorenz E. Löffler, Adam Noble, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

2 Citations (Scopus)

Abstract

Oxidative palladium-catalyzed reaction conditions have been developed to allow for regioselective and stereoselective coupling of allylic boronic esters with a range of carbon-, oxygen-, and nitrogen-based nucleophiles. Studies into the mechanism of the reaction have shown that the key transmetalation step occurs with retention of stereochemistry, since overall inversion is observed.

Original languageEnglish
Article numberst-2015-b0205-l
Pages (from-to)1567-1572
Number of pages6
JournalSYNLETT
Volume26
Issue number11
DOIs
Publication statusPublished - 1 Jul 2015

Structured keywords

  • BCS and TECS CDTs

Keywords

  • allylation
  • boronic ester
  • oxidative coupling
  • palladium
  • umpolung

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