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We found that 1,1,1,3,3,3\u2010hexafluoro\u20102\u2010propanol (HFIP) is the solvent of choice for this transformation, as it outcompetes the usual solvents in terms of rate and yield. Side reactions and other issues raised by the title reaction are prevented, thereby providing an avenue to complex molecules that were previously inaccessible. Lewis acidity studies and computations were carried out to unveil the role of HFIP. Based on these results, we propose that HFIP is, in fact, acting as a Lewis acid and that its acidity can be enhanced when combined with a calcium(II) salt.<\/jats:p>","DOI":"10.1002\/chem.201603592","type":"journal-article","created":{"date-parts":[[2016,10,4]],"date-time":"2016-10-04T20:10:55Z","timestamp":1475611855000},"page":"16165-16171","source":"Crossref","is-referenced-by-count":89,"title":["Harnessing the Lewis Acidity of HFIP through its Cooperation with a Calcium(II) Salt: Application to the Aza\u2010Piancatelli Reaction"],"prefix":"10.1002","volume":"22","author":[{"given":"David","family":"Leb\u0153uf","sequence":"first","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire et des Mat\u00e9riaux d'Orsay (ICMMO) CNRS UMR 8182 Universit\u00e9 Paris-Sud Universit\u00e9 Paris-Saclay  B\u00e2timent\u2005420 91405 Orsay cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucile","family":"Marin","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire et des Mat\u00e9riaux d'Orsay (ICMMO) CNRS UMR 8182 Universit\u00e9 Paris-Sud Universit\u00e9 Paris-Saclay  B\u00e2timent\u2005420 91405 Orsay cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bastien","family":"Michelet","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire et des Mat\u00e9riaux d'Orsay (ICMMO) CNRS UMR 8182 Universit\u00e9 Paris-Sud Universit\u00e9 Paris-Saclay  B\u00e2timent\u2005420 91405 Orsay cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alejandro","family":"Perez\u2010Luna","sequence":"additional","affiliation":[{"name":"Sorbonne Universit\u00e9s UPMC Univ. Paris\u20056 Institut Parisien de Chimie Mol\u00e9culaire (IPCM) CNRS UMR 8232  4, place Jussieu 75005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"R\u00e9gis","family":"Guillot","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire et des Mat\u00e9riaux d'Orsay (ICMMO) CNRS UMR 8182 Universit\u00e9 Paris-Sud Universit\u00e9 Paris-Saclay  B\u00e2timent\u2005420 91405 Orsay cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emmanuelle","family":"Schulz","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire et des Mat\u00e9riaux d'Orsay (ICMMO) CNRS UMR 8182 Universit\u00e9 Paris-Sud Universit\u00e9 Paris-Saclay  B\u00e2timent\u2005420 91405 Orsay cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1108-9410","authenticated-orcid":false,"given":"Vincent","family":"Gandon","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire et des Mat\u00e9riaux d'Orsay (ICMMO) CNRS UMR 8182 Universit\u00e9 Paris-Sud Universit\u00e9 Paris-Saclay  B\u00e2timent\u2005420 91405 Orsay cedex France"},{"name":"Institut de Chimie des Substances Naturelles (ICSN) CNRS UPR 2301 Universit\u00e9 Paris-Sud Universit\u00e9 Paris-Saclay  1, av. de la Terrasse 91198 Gif-sur-Yvette France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,9,30]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1340414"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500504w"},{"key":"e_1_2_6_4_1","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.04.014"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.05.019"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500005"},{"key":"e_1_2_6_8_2","first-page":"732","volume":"12","author":"Nakanishi N.","year":"2009","journal-title":"Curr. 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