A pragmatic procedure for predicting regioselectivity in nucleophilic substitution of aromatic fluorides

作者：Liljenberg Magnus; Brinck Tore^*; Herschend Bjorn; Rein Tobias; Rockwell Glen; Svensson Mats

来源：Tetrahedron Letters, 2011, 52(24): 3150-3153.

DOI：10.1016/j.tetlet.2011.04.032

• Nucleophilic substitution
• Regioselectivity
• Computational
• sigma-Complex
• DFT

The scope and limitations of a method for predicting the regioisomer distribution in kinetically controlled nucleophilic substitution reactions of aromatic fluorides have been investigated. This method is based on calculating the relative stabilities of the isomeric sigma-complex intermediates using OFT. A wide set of substrates and anionic nucleophiles have been investigated. Predictions from this method can be used quantitatively-these agree to an average accuracy of +/-0.5 kcal/mol with experimental observations in eleven of the twelve investigated reactions.

• 出版日期2011-6-15