23 Jan 2017

Reactivity of a platinum benzyne compound

Literature Discussion

Submitted by Chip Nataro, Lafayette College

The literature discussion is based on a paper by Gagné (Organometallics 2015, 34, 2707).  In this work, the in situ generation of benzyne is examined. The benzyne coordinates to a platinum center with a tridentate (pincer) phosphine ligand and a methyl group. This provides an opportunity to discuss the characterization of compounds that have NMR active nuclei that are not 100% naturally abundant. Protonation of the benzyne compound results in the formation of toluene. Different mechanisms are considered.

File Questions for students19.83 KB
Learning Goals: 

Upon completing this LO students should be able to 

  1. Describe what benzyne is and how it is formed
  2. Explain the coordination of benzyne (and therefore all alkynes) as L type donors to a metal center
  3. Use the CBC method to count electrons in all of the compounds and intermediates in this study
  4. Rationalize reaction pathways using electron counting techniques
  5. Explain 195Pt satellites
Time Required: 
50 minutes or so
Evaluation Methods: 

This was developed after the semester in which I teach this material. I look forward to using it next fall and I hope to post some evaluation data at that point.

Creative Commons License: 
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