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Harnessing the Lewis Acidity of HFIP through its Cooperation with a Calcium(II) Salt: Application to the Aza‐Piancatelli Reaction
Author(s) -
Lebœuf David,
Marin Lucile,
Michelet Bastien,
PerezLuna Alejandro,
Guillot Régis,
Schulz Emmanuelle,
Gandon Vincent
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603592
Subject(s) - salt (chemistry) , lewis acids and bases , chemistry , solvent , yield (engineering) , transformation (genetics) , scope (computer science) , calcium , molecule , combinatorial chemistry , computational chemistry , catalysis , organic chemistry , materials science , biochemistry , computer science , metallurgy , gene , programming language
A method to extend the scope of the aza‐Piancatelli reaction between 2‐furylcarbinols and anilines is depicted. We found that 1,1,1,3,3,3‐hexafluoro‐2‐propanol (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.