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Mild Double Allylboration Reactions of Nitriles and Acid Anhydrides Using Potassium Allyltrifluoroborate

Timothy R. Ramadhar, Jazmin Bansagi and Robert A. Batey*

*Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, Canada, M5S 3H6, Email: rbateychem.utoronto.ca

T. R. Ramadhar, J. Bansagi, R. A. Batey, J. Org. Chem., 2013, 78, 1216-1221.

DOI: 10.1021/jo302194n (free Supporting Information)



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Abstract

A mild and chemoselective 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 reaction with an operationally stable and robust potassium organotrifluoroborate reagent avoids the use of metals.

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Key Words

Homoallylamines


ID: J42-Y2013-0330