Reactivity of M-C bonds and catalytic formation of heterocycles

Reactivity of M-C bonds and catalytic formation of heterocycles

There are two tasks, one is writing up a brief report about the topic of the project, and the other one is making a work plan describing experiments to be carried out. And please use font size 11 and Arial. With the layout used in the word document I have attached.

Write 3 pages for the brief report and 4 pages for the work plan with as much detail as you can. Please forget the cover and blank pages at the beginning and the end of the work as I will do the page layout myself.

Tasks
1. Write a brief report (2-3 pages) outlining the key background to the project (CH activation, particularly AMLA/CMD, some on catalysis with heterocycles)
2. Construct a work plan, describing experiments to be carried out. Include ideas on how to synthesise ligands and preparation of metal complexes. Give some idea of how much you might expect to do before xmas


Referencing Requirements:
1. G. Song, F. Wang and X. Li, Chem. Soc. Rev., 2012, 41, 3651-3678
2. Y. Boutadla, D. L. Davies, O. Al-Duaij, J. Fawcett, R. C. Jones and K. Singh, Dalton Trans., 2010, 39, 10447-10457
3. Y. Boutadla, D. L. Davies, S. A. Macgregor and A. I. Poblador-Bahamonde, Dalton Trans., 2009, 5820-5831.
Reactivity of M-C bonds and catalyticformation ofheterocycles
Aims: The aims of this project are to make some ligands containing heterocycles (or vinyl groups)which can undergo CH activation to form cyclometallated complexes and then investigate the reactivity of the cyclometallated complexes with alkynes and alkenes. The goal is to assess the relative reactivity of different types of CMC bonds.

Background
Cyclometallation by an ambiphilic metal ligand activation (AMLA) process is now well established and is used in many catalytic cycles.1 The CH activation step involves activation by an electrophilic metal combined with deprotonation by an intramolecular base, usually acetate. To date the vast majority of examples (>95%) involve activation of a phenyl group. We have recently studied the relative ease of activation of different types of CH bond, e.g. heterocycles in ligands 1 X = O,S, NH or NR, or activation of a vinyl group to form (2) [M(ring) = RhCp*, IrCp* or Ru(p-cymene)].
After CH activation the cyclometallated products 2 can react with unsaturated species such as alkynes. The effect of the different M-C bond (from phenyl, heterocycle or vinyl) on the ease of insertion with alkynes to form 3 has not been studied previously.  Similarly the effect on the end products in catalysis e.g. 4 has not been examined.
This project will involve the synthesis of different complexes 2 and study of their reactions with various alkynes to form 3 or 4. In this project the experimental results will be compared with the results predicted by computational chemistry carried out by collaborators at Heriott Watt University.

Objectives
1. Prepare functionalised heterocycles e.g. 1and cyclometallated complexes 2
2. Investigate reactivity of 2 with alkynes to form 3/4
3 Investigate catalytic reactivity of 2 with alkynes
4 Try reactions with different directing groups (e.g. pyridine in place of imine) and/or with the directing group in a different position on the heterocycle.

Reading
1.    G. Song, F. Wang and X. Li, Chem. Soc. Rev., 2012, 41, 3651-3678
2    Y. Boutadla, D. L. Davies, O. Al-Duaij, J. Fawcett, R. C. Jones and K. Singh, Dalton Trans., 2010, 39, 10447-10457
3    Y. Boutadla, D. L. Davies, S. A. Macgregor and A. I. Poblador-Bahamonde, Dalton Trans., 2009, 5820-5831.

key concepts
1. CH activation
2 Heterocyclesynthesis by oxidative catalysis
3 AMLA and CMD (Concerted metallationdeprotonation)

Tasks
1. Write a brief report (2-3 pages) outlining the key background to the project (CH activation, particularly AMLA/CMD, some on catalysis with heterocycles)
2. Construct a work plan, describing experiments to be carried out. Include ideas on how to synthesise ligands and preparation of metal complexes. Give some idea of how much you might expect to do before xmas

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