<?xml version="1.0" encoding="ISO-8859-1"?><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
<front>
<journal-meta>
<journal-id>0187-893X</journal-id>
<journal-title><![CDATA[Educación química]]></journal-title>
<abbrev-journal-title><![CDATA[Educ. quím]]></abbrev-journal-title>
<issn>0187-893X</issn>
<publisher>
<publisher-name><![CDATA[Universidad Nacional Autónoma de México, Facultad de Química]]></publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id>S0187-893X2017000100005</article-id>
<article-id pub-id-type="doi">10.1016/j.eq.2016.10.001</article-id>
<title-group>
<article-title xml:lang="pt"><![CDATA[N-arilação do imidazol via CuI: um tutorial para otimização de um sistema catalítico através do planejamento experimental]]></article-title>
<article-title xml:lang="en"><![CDATA[N-arylation of the imidazole via Cul: A tutorial for optimization of a catalytic system through of experimental design]]></article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Silveira]]></surname>
<given-names><![CDATA[Márcia Victória]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Lopes]]></surname>
<given-names><![CDATA[Toni Jefferson]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Rosa]]></surname>
<given-names><![CDATA[Gilber Ricardo]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
</contrib-group>
<aff id="Af1">
<institution><![CDATA[,Universidade Federal do Rio Grande Escola de Química e Alimentos ]]></institution>
<addr-line><![CDATA[Santo Antônio da Patrulha RS]]></addr-line>
<country>Brasil</country>
</aff>
<pub-date pub-type="pub">
<day>00</day>
<month>00</month>
<year>2017</year>
</pub-date>
<pub-date pub-type="epub">
<day>00</day>
<month>00</month>
<year>2017</year>
</pub-date>
<volume>28</volume>
<numero>1</numero>
<fpage>44</fpage>
<lpage>50</lpage>
<copyright-statement/>
<copyright-year/>
<self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_arttext&amp;pid=S0187-893X2017000100005&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_abstract&amp;pid=S0187-893X2017000100005&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_pdf&amp;pid=S0187-893X2017000100005&amp;lng=en&amp;nrm=iso"></self-uri><abstract abstract-type="short" xml:lang="pt"><p><![CDATA[Resumo: Este trabalho trata do desenvolvimento de um sistema catalítico para a N-arilação do imidazol, com CuI, através do planejamento experimental. A 1.10-fenantrolina (ligante bidentado) foi utilizada e provou ser eficaz no acoplamento de iodo e bromoarenos com imidazol. Assim, o artigo aqui apresentado está destinado a servir como um tutorial para a otimização de novos sistemas catalíticos e pode ser aplicado como uma aula prática de baixo custo para estudantes universitários de química.]]></p></abstract>
<abstract abstract-type="short" xml:lang="en"><p><![CDATA[Abstract: This work deals the development of a catalytic system for the N-arylation of imidazole with CuI through experimental design. 1,10-Phenanthroline (bidentate ligand) was used and proved to be efficient in the coupling of iodo- and bromoarenes with imidazole. Thus, the article presented here is intended to serve as a tutorial for optimization of new catalytic systems and may be applied as a lowcost practical class for chemistry undergraduate students.]]></p></abstract>
<kwd-group>
<kwd lng="pt"><![CDATA[Imidazol]]></kwd>
<kwd lng="pt"><![CDATA[CuI]]></kwd>
<kwd lng="pt"><![CDATA[Planejamento experimental]]></kwd>
<kwd lng="en"><![CDATA[Imidazole]]></kwd>
<kwd lng="en"><![CDATA[CuI]]></kwd>
<kwd lng="en"><![CDATA[Experimental design]]></kwd>
</kwd-group>
</article-meta>
</front><back>
<ref-list>
<ref id="B1">
<nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Barros-Neto]]></surname>
<given-names><![CDATA[B.]]></given-names>
</name>
<name>
<surname><![CDATA[Scarminio]]></surname>
<given-names><![CDATA[I. S.]]></given-names>
</name>
<name>
<surname><![CDATA[Bruns]]></surname>
<given-names><![CDATA[R. E.]]></given-names>
</name>
</person-group>
<source><![CDATA[Planejamento e otimização de experimentos]]></source>
<year>1995</year>
<publisher-loc><![CDATA[Campinas, Brasil ]]></publisher-loc>
<publisher-name><![CDATA[Editora UNICAMP]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B2">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Belcher]]></surname>
<given-names><![CDATA[R.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[The application of chelate compounds in analytical chemistry]]></article-title>
<source><![CDATA[Pure and Applied Chemistry]]></source>
<year>1973</year>
<volume>34</volume>
<numero>1</numero>
<issue>1</issue>
<page-range>13-28</page-range></nlm-citation>
</ref>
<ref id="B3">
<nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Box]]></surname>
<given-names><![CDATA[G. E. P.]]></given-names>
</name>
<name>
<surname><![CDATA[Hunter]]></surname>
<given-names><![CDATA[J. S.]]></given-names>
</name>
<name>
<surname><![CDATA[Hunter]]></surname>
<given-names><![CDATA[W. G.]]></given-names>
</name>
</person-group>
<source><![CDATA[Statistics for Experimenters: Design, Innovation, and Discovery]]></source>
<year>2005</year>
<publisher-loc><![CDATA[Michigan, EUA ]]></publisher-loc>
<publisher-name><![CDATA[Wiley-Interscience]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B4">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Dalmás]]></surname>
<given-names><![CDATA[M.]]></given-names>
</name>
<name>
<surname><![CDATA[Moura]]></surname>
<given-names><![CDATA[N. F.]]></given-names>
</name>
<name>
<surname><![CDATA[Rosa]]></surname>
<given-names><![CDATA[G. R.]]></given-names>
</name>
<name>
<surname><![CDATA[Ferreira]]></surname>
<given-names><![CDATA[C. L.]]></given-names>
</name>
<name>
<surname><![CDATA[Santos]]></surname>
<given-names><![CDATA[J. A. O.]]></given-names>
</name>
<name>
<surname><![CDATA[Bolzan]]></surname>
<given-names><![CDATA[T. K.]]></given-names>
</name>
<name>
<surname><![CDATA[Kokubun]]></surname>
<given-names><![CDATA[F.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Mini-project for teaching experimental organic chemistry based on N-C cross-coupling promoted by microwave]]></article-title>
<source><![CDATA[Química Nova]]></source>
<year>2013</year>
<volume>36</volume>
<numero>9</numero>
<issue>9</issue>
<page-range>1464-7</page-range></nlm-citation>
</ref>
<ref id="B5">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Driver]]></surname>
<given-names><![CDATA[M. S.]]></given-names>
</name>
<name>
<surname><![CDATA[Hartwig]]></surname>
<given-names><![CDATA[J. F.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[A second-generation catalyst for aryl halide amination: Mixed secondary amines from aryl halides and primary amines catalyzed by (DPPF)PdCl2]]></article-title>
<source><![CDATA[Journal of the American Chemical Society]]></source>
<year>1996</year>
<volume>118</volume>
<numero>30</numero>
<issue>30</issue>
<page-range>7217-8</page-range></nlm-citation>
</ref>
<ref id="B6">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Giri]]></surname>
<given-names><![CDATA[R.]]></given-names>
</name>
<name>
<surname><![CDATA[Hartwig]]></surname>
<given-names><![CDATA[J. F.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Cu(I)&#8722;amido complexes in the Ullmann Reaction: Reactions of Cu(I)&#8722;amido complexes with iodoarenes with and without autocatalysis by CuI]]></article-title>
<source><![CDATA[Journal of the American Chemical Society]]></source>
<year>2010</year>
<volume>132</volume>
<numero>45</numero>
<issue>45</issue>
<page-range>15860-3</page-range></nlm-citation>
</ref>
<ref id="B7">
<nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Greenstein]]></surname>
<given-names><![CDATA[J. P.]]></given-names>
</name>
<name>
<surname><![CDATA[Winitz]]></surname>
<given-names><![CDATA[M.]]></given-names>
</name>
</person-group>
<source><![CDATA[Chemistry of the Amino Acids]]></source>
<year>1961</year>
<publisher-loc><![CDATA[Nova Iorque, EUA ]]></publisher-loc>
<publisher-name><![CDATA[Wiley]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B8">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Guram]]></surname>
<given-names><![CDATA[A. S.]]></given-names>
</name>
<name>
<surname><![CDATA[Rennels]]></surname>
<given-names><![CDATA[R. A.]]></given-names>
</name>
<name>
<surname><![CDATA[Buchwald]]></surname>
<given-names><![CDATA[S. L.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[A simple catalytic method for the conversion of aryl bromides to arylamines]]></article-title>
<source><![CDATA[Angewandte Chemie- International Edition in English]]></source>
<year>1995</year>
<volume>34</volume>
<numero>12</numero>
<issue>12</issue>
<page-range>1348-50</page-range></nlm-citation>
</ref>
<ref id="B9">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Hamann]]></surname>
<given-names><![CDATA[B. C.]]></given-names>
</name>
<name>
<surname><![CDATA[Hartwig]]></surname>
<given-names><![CDATA[J. F.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates]]></article-title>
<source><![CDATA[Journal of the American Chemical Society]]></source>
<year>1998</year>
<volume>120</volume>
<numero>29</numero>
<issue>29</issue>
<page-range>7369-70</page-range></nlm-citation>
</ref>
<ref id="B10">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Hartwig]]></surname>
<given-names><![CDATA[J. F.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Electronic effects on reductive elimination to form carbon-carbon and carbon-heteroatom bonds from palladium(II) complexes]]></article-title>
<source><![CDATA[Inorganic Chemistry]]></source>
<year>2007</year>
<volume>46</volume>
<numero>6</numero>
<issue>6</issue>
<page-range>1936-47</page-range></nlm-citation>
</ref>
<ref id="B11">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Huang]]></surname>
<given-names><![CDATA[Y.-Z.]]></given-names>
</name>
<name>
<surname><![CDATA[Gao]]></surname>
<given-names><![CDATA[J.]]></given-names>
</name>
<name>
<surname><![CDATA[Ma]]></surname>
<given-names><![CDATA[H.]]></given-names>
</name>
<name>
<surname><![CDATA[Miao]]></surname>
<given-names><![CDATA[H.]]></given-names>
</name>
<name>
<surname><![CDATA[Xu]]></surname>
<given-names><![CDATA[J.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Ninhydrin: an efficient ligand for the Cu-catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides]]></article-title>
<source><![CDATA[Tetrahedron Letters]]></source>
<year>2008</year>
<volume>49</volume>
<numero>6</numero>
<issue>6</issue>
<page-range>948-51</page-range></nlm-citation>
</ref>
<ref id="B12">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Li]]></surname>
<given-names><![CDATA[X.]]></given-names>
</name>
<name>
<surname><![CDATA[Yang]]></surname>
<given-names><![CDATA[D.]]></given-names>
</name>
<name>
<surname><![CDATA[Jiang]]></surname>
<given-names><![CDATA[Y.]]></given-names>
</name>
<name>
<surname><![CDATA[Fu]]></surname>
<given-names><![CDATA[H.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Efficient copper-catalyzed N-arylations of nitrogen-containing heterocycles and aliphatic amines in water]]></article-title>
<source><![CDATA[Green Chemistry]]></source>
<year>2010</year>
<volume>12</volume>
<numero>6</numero>
<issue>6</issue>
<page-range>1097-105</page-range></nlm-citation>
</ref>
<ref id="B13">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Louie]]></surname>
<given-names><![CDATA[J.]]></given-names>
</name>
<name>
<surname><![CDATA[Hartwig]]></surname>
<given-names><![CDATA[J. F.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Palladium-catalyzed synthesis of arylamines from aryl halides - mechanistic studies lead to coupling in the absence of tin reagents]]></article-title>
<source><![CDATA[Tetrahedron Letters]]></source>
<year>1995</year>
<volume>36</volume>
<numero>21</numero>
<issue>21</issue>
<page-range>3609-12</page-range></nlm-citation>
</ref>
<ref id="B14">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Mao]]></surname>
<given-names><![CDATA[J.]]></given-names>
</name>
<name>
<surname><![CDATA[Hua]]></surname>
<given-names><![CDATA[Q.]]></given-names>
</name>
<name>
<surname><![CDATA[Guo]]></surname>
<given-names><![CDATA[J.]]></given-names>
</name>
<name>
<surname><![CDATA[Shi]]></surname>
<given-names><![CDATA[D.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Natural alkaloids for copper-catalyzed N-arylation of amines and nitrogen-containing heterocycles]]></article-title>
<source><![CDATA[Catalysis Communications]]></source>
<year>2008</year>
<volume>10</volume>
<numero>3</numero>
<issue>3</issue>
<page-range>341-6</page-range></nlm-citation>
</ref>
<ref id="B15">
<nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Montgomery]]></surname>
<given-names><![CDATA[D. C.]]></given-names>
</name>
</person-group>
<source><![CDATA[Design and Analysis of Experiments]]></source>
<year>1991</year>
<publisher-loc><![CDATA[Nova Iorque, EUA ]]></publisher-loc>
<publisher-name><![CDATA[Wiley]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B16">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Oliveira]]></surname>
<given-names><![CDATA[D. G. M.]]></given-names>
</name>
<name>
<surname><![CDATA[Rosa]]></surname>
<given-names><![CDATA[C. H.]]></given-names>
</name>
<name>
<surname><![CDATA[Vargas]]></surname>
<given-names><![CDATA[B. P.]]></given-names>
</name>
<name>
<surname><![CDATA[Rosa]]></surname>
<given-names><![CDATA[D. S.]]></given-names>
</name>
<name>
<surname><![CDATA[Silveira]]></surname>
<given-names><![CDATA[M. V.]]></given-names>
</name>
<name>
<surname><![CDATA[de Moura]]></surname>
<given-names><![CDATA[N. F.]]></given-names>
</name>
<name>
<surname><![CDATA[Rosa]]></surname>
<given-names><![CDATA[G. R.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Introducing undergraduates to research using a Suzuki-Miyaura cross-coupling organic chemistry miniproject]]></article-title>
<source><![CDATA[Journal of Chemical Education]]></source>
<year>2015</year>
<volume>92</volume>
<numero>7</numero>
<issue>7</issue>
<page-range>1217-20</page-range></nlm-citation>
</ref>
<ref id="B17">
<nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Rodrigues]]></surname>
<given-names><![CDATA[M. I.]]></given-names>
</name>
<name>
<surname><![CDATA[Iemma]]></surname>
<given-names><![CDATA[A. F.]]></given-names>
</name>
</person-group>
<source><![CDATA[Planejamento de experimentos e otimização de processos]]></source>
<year>2009</year>
<publisher-loc><![CDATA[Campinas, Brasil ]]></publisher-loc>
<publisher-name><![CDATA[AMIC]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B18">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Souza]]></surname>
<given-names><![CDATA[A. M.]]></given-names>
</name>
<name>
<surname><![CDATA[Poppi]]></surname>
<given-names><![CDATA[R. J.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Teaching experiment of chemometrics for exploratory analysis of edible vegetable oils by mid infrared spectroscopy and principal component analysis: A tutorial. Part I]]></article-title>
<source><![CDATA[Química Nova]]></source>
<year>2012</year>
<volume>35</volume>
<numero>1</numero>
<issue>1</issue>
<page-range>223-9</page-range></nlm-citation>
</ref>
<ref id="B19">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Vicentini]]></surname>
<given-names><![CDATA[F. C.]]></given-names>
</name>
<name>
<surname><![CDATA[Figueiredo-Filho]]></surname>
<given-names><![CDATA[L. C. S.]]></given-names>
</name>
<name>
<surname><![CDATA[Janegitz]]></surname>
<given-names><![CDATA[B. C.]]></given-names>
</name>
<name>
<surname><![CDATA[Santiago]]></surname>
<given-names><![CDATA[A.]]></given-names>
</name>
<name>
<surname><![CDATA[Pereira-Filho]]></surname>
<given-names><![CDATA[E. R.]]></given-names>
</name>
<name>
<surname><![CDATA[Fatibello-Filho]]></surname>
<given-names><![CDATA[O.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Factorial design and response surface: Voltammetric method optimization for the determination of Ag(I) employing a carbon nanotubes paste electrode]]></article-title>
<source><![CDATA[Química Nova]]></source>
<year>2011</year>
<volume>34</volume>
<numero>5</numero>
<issue>5</issue>
<page-range>825-30</page-range></nlm-citation>
</ref>
<ref id="B20">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Wolfe]]></surname>
<given-names><![CDATA[J. P.]]></given-names>
</name>
<name>
<surname><![CDATA[Wagaw]]></surname>
<given-names><![CDATA[S.]]></given-names>
</name>
<name>
<surname><![CDATA[Buchwald]]></surname>
<given-names><![CDATA[S. L.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[An improved catalyst system for aromatic carbon-nitrogen bond formation: The possible involvement of bis(phosphine) palladium complexes as key intermediates]]></article-title>
<source><![CDATA[Journal of the American Chemical Society]]></source>
<year>1996</year>
<volume>118</volume>
<numero>30</numero>
<issue>30</issue>
<page-range>7215-6</page-range></nlm-citation>
</ref>
<ref id="B21">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Zhang]]></surname>
<given-names><![CDATA[H.]]></given-names>
</name>
<name>
<surname><![CDATA[Cai]]></surname>
<given-names><![CDATA[Q.]]></given-names>
</name>
<name>
<surname><![CDATA[Ma]]></surname>
<given-names><![CDATA[D.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles]]></article-title>
<source><![CDATA[Journal of Organic Chemistry]]></source>
<year>2005</year>
<volume>70</volume>
<numero>13</numero>
<issue>13</issue>
<page-range>5164-73</page-range></nlm-citation>
</ref>
<ref id="B22">
<nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Zhu]]></surname>
<given-names><![CDATA[L.]]></given-names>
</name>
<name>
<surname><![CDATA[Li]]></surname>
<given-names><![CDATA[G.]]></given-names>
</name>
<name>
<surname><![CDATA[Luo]]></surname>
<given-names><![CDATA[L.]]></given-names>
</name>
<name>
<surname><![CDATA[Guo]]></surname>
<given-names><![CDATA[P.]]></given-names>
</name>
<name>
<surname><![CDATA[Lan]]></surname>
<given-names><![CDATA[J.]]></given-names>
</name>
<name>
<surname><![CDATA[You]]></surname>
<given-names><![CDATA[J.]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Highly functional group tolerance in copper-catalyzed N-arylation of nitrogen-containing heterocycles under mild conditions]]></article-title>
<source><![CDATA[Journal of Organic Chemistry]]></source>
<year>2009</year>
<volume>74</volume>
<numero>5</numero>
<issue>5</issue>
<page-range>2200-2</page-range></nlm-citation>
</ref>
</ref-list>
</back>
</article>
