17 Jul 2012

Oxidative Suzuki-Type C-H Functionalization (Learning to Read a Detailed Organic Paper)

Literature Discussion

Submitted by Matt Whited, Carleton College

This is a literature excercise I used in my upper-level organometallic course to guide students through some of the important points of a detailed organic/organometallic paper.  I have found that the first hurdles in some of these papers involve getting students to the point where they can understand (a) what specific reaction is being performed, and (b) what the role of each reagent is.  This set of questions includes a mix of material, including some things that are specifically stated in the article and some that are implied or referenced elsewhere.  I found that excercises like this one, although time-intensive, really helped my students to gain confidence about reading long papers.

I assigned this as a problem set and strongly encouraged collaborative work, although I have also used similar exercises where I assigned the paper as pre-class reading and sent out some or all of the questions in advance, then had them work in groups in class and present their answers to specific questions.

Learning Goals: 
  • The primary goal is for students to gain comfort and familiarity with the primary literature, in this instance a relatively long organic/organometallic paper.
  • A student should be able to read a paper containing a complicated organometallic reaction with many reagents and determine the role of each reagent and the overall transformation being promoted.
  • A student should be able to apply knowledge of periodic trends and basic organic chemistry to rationalize reactivity across a series of substrates, ligands, etc.
Implementation Notes: 

I have given this assignment once (the paper only came out last year), but got very positive feedback from the students.  It was assigned toward the end of a term-long organometallic chemistry course, during which the students had read quite a few (10-15) papers from the primary literature.  This was the longest paper assigned, and I did it with the goal of helping students to pull out important inorganic/organometallic information from a paper written by primarily synthetic organic chemists.

Students had a bit of trouble with a few of the problems, namely 4, 7, and 8 (which do not have suggestions directly in the text).  However, in the end they all performed well on the assignment and I suspect I will tweak this same literature exercise for the next time around.

Time Required: 
Variable (30-40 minutes in class if paper has already been read)
Evaluation Methods: 

This was a problem set graded on a 10-point scale (1 point per question).

If used as a classroom exercise, I would grade primarily on participation within groups and on the willingness of each group to attempt answering questions (and asking further questions).

Evaluation Results: 

With some help from me, the scores generally ranged from 8-10 (out of 10).  I did not encounter any major misconceptions, though I did need to direct several students to ref. 25 (the Sanford/Mayer paper on oxidatively induced reductive elimination from Pd(II), which they found very helpful).

Creative Commons License: 
Creative Commons Licence


This is a nice LO. I hope to use it in my organometallics class this fall.

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