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

H. Christensen; Søren Kiil; Kim Dam-Johansen; O. Nielsen; M.B. Sommer

doi:10.1021/op050226s

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

H. Christensen, Søren Kiil, Kim Dam-Johansen, O. Nielsen, M.B. Sommer

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

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.

Original language	English
Journal	Organic Process Research and Development
Volume	10
Issue number	4
Pages (from-to)	762-769
ISSN	1083-6160
DOIs	https://doi.org/10.1021/op050226s
Publication status	Published - 2006

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title = "Effect of Solvents on the Product Distribution and Reaction Rate of a Buchwald-Hartwig Amination Reaction",

abstract = "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. ",

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T1 - Effect of Solvents on the Product Distribution and Reaction Rate of a Buchwald-Hartwig Amination Reaction

AU - Christensen, H.

AU - Kiil, Søren

AU - Dam-Johansen, Kim

AU - Nielsen, O.

AU - Sommer, M.B.

PY - 2006

Y1 - 2006

N2 - 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.

AB - 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.

U2 - 10.1021/op050226s

DO - 10.1021/op050226s

M3 - Journal article

SN - 1083-6160

VL - 10

SP - 762

EP - 769

JO - Organic Process Research and Development

JF - Organic Process Research and Development

IS - 4

ER -

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

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