Effect of Solvents on the Product Distribution and Reaction Rate of a Buchwald−Hartwig Amination Reaction

✍ Scribed by Christensen, Henrik; Kiil, Søren; Dam-Johansen, Kim; Nielsen, Ole; Sommer, Michael B.

• Book ID: 120243744
• Publisher: American Chemical Society
• Year: 2006
• Tongue: English
• Weight: 163 KB
• Volume: 10
• Category: Article
• ISSN: 1083-6160
• DOI: 10.1021/op050226s

✦ Synopsis

The Buchwald-Hartwig amination reaction between p-bromotoluene and piperazine in the presence of the homogeneous catalytic system Pd(dba) 2 /(()-BINAP and the base NaO-t-Bu was investigated in two different classes of solvents: aprotic, nonpolar and aprotic, polar. The reaction was carried out using microwaves as the heating source, and it was found that the product distribution was strongly dependent on the class of the solvent. Based on the experimental results the selectivity towards the desired monosubstituted aryl piperazine was calculated, and it was found that the most appropriate solvent for the Buchwald-Hartwig amination reaction under the conditions applied was m-xylene.