New roles for old actors

There are several reasons, some of which are top secret in nature, that lead me to say that I am very interested in the chemistry reported by Xiao and colleagues in the Org. Lett. paper shown below. I like this work because it showcases a rather mundane solvent (dimethylformamide, or DMF) in an unusual role: that of a methyl group donor. The way this chemistry occurs is by a process that involves oxidation of DMF into an N-formyl iminium cation, followed by a Mannich-type reaction. There is a nice scope of substrates in this work and I am not even focusing on what really matters to the authors – the metal catalysis part – but I just don’t have time (I am about to barbeque a juicy slice of pork, as part of a dress rehearsal for this Sunday’s lab get-together at our place)… Anyhow, Dr. Xiao and colleagues are to be congratulated on this feat. We need to see more studies that showcase how boring molecules get accustomed to new and exciting roles. Speaking of DMF, even its synthesis can be very cool. I still recall hearing awesome talks by Professor Noyori in the early 1990’s. He would dedicate his whole lecture to the use of hydrogenation catalysis in efforts to make DMF on the cheap. There was something Tom Sawyer-esque in that work (I refer to painting the proverbial fence)…

gg

http://pubs.acs.org/doi/abs/10.1021/ol403040g

2 thoughts on “New roles for old actors

  1. Neat stuff! I like how there are conceptual similarities to the classic Vilsmeier–Haack reaction, but by going through a different iminium ion, the authors are able to use DMF as a methyl rather than formyl source.
    So much versatility from a simple molecule!

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