Journal of Organic Chemistry 2009-06-19

Room-temperature Pd-catalyzed amidation of aryl bromides using tert-butyl carbamate.

Swapna Bhagwanth, Alex G Waterson, George M Adjabeng, Keith R Hornberger

Index: J. Org. Chem. 74(12) , 4634-7, (2009)

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Abstract

The scope of Pd-catalyzed synthesis of N-Boc-protected anilines from aryl bromides and commercially available tert-butyl carbamate is described. For the first time, this process can be conducted at room temperature (17-22 degrees C) using a combination of Pd(2)dba(3).CHCl(3) and a monodentate ligand, tert-butyl X-Phos. Use of sodium tert-butoxide is crucial to the success of the reaction, which proceeds in 43-83% yield.