Collman’s Reagent

• General Characteristics

Disodium tetracarbonylferrate is generally referred to as the Collman reagent. It reacts with alkyl halides to give corresponding aldehydes and ketones.

• General References

• Collman, J. P.; Winter, S. R. J. Am. Chem. Soc. 1973, 95, 4089. DOI: 10.1021/ja00793a066
• Collman, J. P.; Finke, R. G.; Cawse, J. N.; Brauman, J. I. J. Am. Chem. Soc. 1977, 99, 2515. DOI: 10.1021/ja00450a019
• Collman, J. P. Acc. Chem. Res. 1975, 8, 342. DOI: 10.1021/ar50094a004

• History

Na₂[Fe(CO)₄] complex and its synthetic applications were reported by James Collman in the 1970’s.

• Reaction Mechanism

• Examples

Unsymmetrical ketones can be synthesized by reacting two benzyl halides with the Collman’s reagent sequentially.^[1]

• Experimental Procedure

• Experimental Tips

• References

[1] Potter, R. G.; Hughes, T. S. Org. Lett. 2007, 9, 1187. DOI: 10.1021/ol0629770

• Related Reactions

• Related Books

[amazonjs asin=”189138953X” locale=”US” title=”Organotransition Metal Chemistry: From Bonding to Catalysis”]

• External Links

Disodium Tetracarbonylferrate – Wikipedia

formylation of alkyl halides, iron tetracarbonyl complex, synthesis of aldehydes and ketones