Two things I like to see: Reactions that I don’t often come across and having a functional handle to utilize in some of the chemistry I am interested in…..so imagine my delight in this paper (Molecules 2013) –Efficient Synthesis of Boron-Containing α-Acyloxyamide Analogs via Microwave Irradiation — Boron in the final compound — I can use it again, well all….right (in my Dazed and Confused voice) AND the α-Acyloxyamide which is often formed via a Passerini reaction.

Although this group was actually looking to make boron containing compounds to study cytotoxicity, I thought about the handle that it provided (although pointed out that there is a boron containing compound commercially available as a drug, I can’t imagine non-cancer targets would provide too much opportunity for this functionality.

First things first” Passerini: below

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Multicomponent Passerini reaction (Acid, aldehyde and isocyanide)

Applying this to the aldehyde or the carboxylic acid gives us a way to functionalize two different sides of a fragment — come on you combichemERS.

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Boron on the carboxylic acid

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Boron on the aldehyde starting material

Although not exhaustive, there were a few solvents screened, H2O provided the best set of conditions in the microwave –55C, well maybe not so much. I would have to look into additional solvents and temperatures — must be some hydrolysis somewhere.

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Small solvent screening sample

It’s a quick read, but think about the utility. Could show some potential for adding an additional starting material and coupling post pinacol-boronate formation.

Enjoy!

 

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