Alkynyl ketones – the boron way

I have enjoyed reading Prof. Yuri Bolshan’s paper, recently published in Org. Lett. Yuri hails from the University of Toronto, where he did his PhD under the direction of Professor Robert Batey. Afterwards, Yuri did his postdoctoral studies with Tohru Fukuyama in Tokyo and worked at the Ontario Institute for Cancer Research (OICR) here in Toronto. Right now Yuri is an Assistant Professor at the University of Ontario Institute of Technology (http://sites.uoit.ca/yuri-bolshan/y-bolshan/). What attracted me to the Org. Lett. paper is the symbiotic relationship between two types of boron units: BF3 and BCl3. The BF3 fragment enters the reaction bound to an alkynyl ligand (as the trifluoroborate salt), while BCl3 acts as the Lewis acid promoter. The authors propose several mechanistic possibilities, one of which is shown below. In it, the transiently formed alkyne-BCl2 reagent coordinates to the oxygen center of the acyl chloride component, which triggers alkynyl migration to the carbonyl carbon, ultimately producing the alkynyl ketone product. I want to wish Yuri all the best in his new position. It looks to me that he is off to a nice start!

Image

http://pubs.acs.org/doi/abs/10.1021/ol403370t

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s