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This reaction is strongly dependent on the nature of the counterion. Whereas with BF<jats:sub>4<\/jats:sub><jats:sup>\u2013<\/jats:sup> the reaction proceeds with conversions up to 90\u2009%, in the case of the counterions NO<jats:sub>3<\/jats:sub><jats:sup>\u2013<\/jats:sup>, CF<jats:sub>3<\/jats:sub>COO<jats:sup>\u2013<\/jats:sup>, CF<jats:sub>3<\/jats:sub>SO<jats:sub>3<\/jats:sub><jats:sup>\u2013<\/jats:sup>,SbF<jats:sub>6<\/jats:sub><jats:sup>\u2013<\/jats:sup>, and BAr\u2032<jats:sub>4<\/jats:sub><jats:sup>\u2013<\/jats:sup> [Ar\u2032 = 3,5\u2010(CF<jats:sub>3<\/jats:sub>)<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>3<\/jats:sub>] no reaction took place. In the case of PF<jats:sub>6<\/jats:sub><jats:sup>\u2013<\/jats:sup> only up to 20\u2009% conversion was achieved. A conceivable mechanism for the coupling of aromatic aldehydes with EDA was established by means of DFT\/B3LYP calculations, which allowed the rationalization of both the chemoselectivity and the role of the counterions.<\/jats:p>","DOI":"10.1002\/ejic.201000240","type":"journal-article","created":{"date-parts":[[2010,5,24]],"date-time":"2010-05-24T11:52:14Z","timestamp":1274701934000},"page":"3160-3166","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Unusual Anion Effects in the Iron\u2010Catalyzed Formation of 3\u2010Hydroxyacrylates from Aromatic Aldehydes and Ethyl Diazoacetate"],"prefix":"10.1002","volume":"2010","author":[{"given":"Luis Gon\u00e7alo","family":"Alves","sequence":"first","affiliation":[]},{"given":"Georg","family":"Dazinger","sequence":"additional","affiliation":[]},{"given":"Luis F.","family":"Veiros","sequence":"additional","affiliation":[]},{"given":"Karl","family":"Kirchner","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2010,7,6]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00275a006"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)91877-X"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00305a029"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1996-5417"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00081a035"},{"key":"e_1_2_6_7_2","unstructured":"\u00a0"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo972142q"},{"key":"e_1_2_6_9_2","first-page":"1807","author":"Mahmood S. 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