Organic Chemistry

Boron juggling makes two bonds in a row

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Science  24 Jul 2015:
Vol. 349, Issue 6246, pp. 393-394
DOI: 10.1126/science.349.6246.393-f

Suzuki coupling is a widely used chemical reaction to make carbon-carbon bonds. Essentially, the technique relies on a boron substituent to activate one of the carbon centers. If two different compounds in the mix had C-B bonds, you might expect little control over which one reacted when. Seath et al. now show that by juggling the other groups bound to the boron, they can selectively activate two different C-B linkages sequentially. A timely swapping of methylaminodiacetic acid with pinacol enables selective and efficient coupling of three components in a single reaction mixture.

Angew. Chem. Int. Ed. 10.1002/anie.201504297 (2015).

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