18 Jul 2012

C(sp3)-F Activation through an Initial C(sp3)-H Activation Mechanism

Literature Discussion

Submitted by John Lee, University of Tennessee Chattanooga

This paper is from a Science article from Alan Goldman’s group at Rutgers University. It was one of the literature articles that was assigned during the IONiC VIPEr Workshop in July 2012.  In conjunction with reading the article, workshop participants attended a seminar presented by Alan Goldman on this work.

Here, Goldman’s group showed that C-F bond oxidative addition is possible through an initial C-H bond activation to the (PCP)Ir active complex.  Several key intermediates and Ir complexes were identified using 1H, 13C, 31P and 19F NMR.  LIFDI MS, a soft ionization MS technique, was used to verify the identity of (PCP)Ir(CH3)F.  DFT calculations along with experimental work were used to elucidate a likely mechanism. 

Learning Goals: 

Students should be able to:

  • determine the importance/impact of a paper
  • be able to use cited references within a paper to backtrack both prior and relevant work
  • be able to count electrons for all complexes in this paper
  • be able to describe how spectroscopic techniques are used to characterize new compounds
  • be able to describehow experimental studies are done to determine a reaction mechanism (or disprove a mechanism)
  • be able to describe how computational chemistry, when combined with experimental results, can give more insight into a reaction
Implementation Notes: 

A copy of the paper (and guided questions) should be made available to students at least one week prior to the scheduled literature discussion.  During class, allow students to break up into small groups and compare answers/discuss the paper.  The instructor can walk around the room answering questions.  Interesting questions, both related and unrelated to the guided questions, should be announced to the entire class to allow for further discussion.

Time Required: 
50 minute lecture
Evaluation Methods: 

The guided questions can be collected and graded.  In addition, (or alternatively) a qualitative grade can be given for class participation. 

An exam question has also been posted on VIPEr that can be used.

Creative Commons License: 
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