Mild double allylboration reactions of nitriles and acid anhydrides using potassium allyltrifluoroborate.

J Org Chem

Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, Canada, M5S 3H6.

Published: February 2013

The double allylboration of nitriles and acid anhydrides to form bis-allyl amines and esters, respectively, can be achieved through the use of potassium allyltrifluoroborate in the presence of boron trifluoride etherate at room temperature. The method described is relatively mild, exhibits chemoselectivity to other electrophiles present, avoids the use of metals, and features the use of an operationally stable and robust potassium organotrifluoroborate reagent.

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http://dx.doi.org/10.1021/jo302194nDOI Listing

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