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Markovnikov at Gold: Nucleophilic Addition to Alkenes at Au(III)

Abstract

The reactivity of Au(OAcF)2(tpy) (1, OAcF = OCOCF3; tpy = 2-(p-tolyl)pyridine) toward a wide variety of different alkenes with various substitution patterns and different oxygen-based nucleophiles has been investigated. These reactions are two-step processes where a ligand substitution is followed by a nucleophilic addition furnishing Au(III) complexes with C(sp3) ligands. In this work we have found that the reactions always occur trans to tpy-N while the OAcF ligand remains in place trans to tpy-C. The nucleophilic addition takes place exclusively at the most substituted side of the double bond, in a Markovnikov manner, and the nucleophilic addition occurs in an anti fashion as can be seen from the reaction with the 2,3-disubstituted alkene trans-2-hexene. This study has provided valuable insight into the scope and regiochemistry of Au(III) mediated nucleophilic additions, which is of great importance for further development of Au(III) catalysis and alkene functionalization.
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Category

Academic article

Language

English

Author(s)

  • Marte Sofie Holmsen
  • Franziska Ihlefeldt
  • Sigurd Øien-Ødegaard
  • Eirin Langseth
  • Yannick Wencke
  • Richard H Heyn
  • Mats Tilset

Affiliation

  • SINTEF Industry / Process Technology
  • University of Oslo

Year

2018

Published in

Organometallics

ISSN

0276-7333

Volume

37

Issue

12

Page(s)

1937 - 1947

View this publication at Norwegian Research Information Repository