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The reaction selectivity was found to depend on the amount of the base used, with fewer bases favoring the reactivity of the boronic acid with lower p<jats:italic>K<\/jats:italic><jats:sub>a<\/jats:sub> (stronger acid). The dependence of the reaction selectivity on base stoichiometry was found to increase with the increase in the difference in the p<jats:italic>K<\/jats:italic><jats:sub>a<\/jats:sub> values of the competing boronic acids. These results confirm a relationship between acid\u2013base chemistry and the Suzuki\u2013Miyaura reaction catalytic cycle. Moreover, the results indicate that under these specific conditions, the most reactive organoboron species toward transmetalation is the borate anion R\uf8ffB(OH)<jats:sub>3<\/jats:sub><jats:sup>\u2212<\/jats:sup> instead of the neutral boronic acid R\uf8ffB(OH)<jats:sub>2<\/jats:sub>. Hence, the main role of the base in the reaction mechanism is to increase the reactivity of the boronic acid toward the Pd\u2013halide complex by converting it into the respective organoborate. In addition, boric acid, an important reaction byproduct, affects the selectivity in the Suzuki reaction because its gradual formation in the reaction medium disturbs the acid\u2013base equilibrium.<\/jats:p>","DOI":"10.1002\/cctc.201301080","type":"journal-article","created":{"date-parts":[[2014,3,12]],"date-time":"2014-03-12T08:47:22Z","timestamp":1394614042000},"page":"1291-1302","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":93,"title":["Role of the Base and Control of Selectivity in the Suzuki\u2013Miyaura Cross\u2010Coupling Reaction"],"prefix":"10.1002","volume":"6","author":[{"given":"Carlos F. R. A. C.","family":"Lima","sequence":"first","affiliation":[]},{"given":"Ana S. M. 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