Open AccessAsymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis
Author(s) -
Gabriele Pupo,
Francesco Ibba,
David M. H. Ascough,
Anna Chiara Vicini,
Paolo F. Ricci,
Kirsten E. Christensen,
Lukas Pfeifer,
J. Richard Morphy,
John M. Brown,
Robert S. Paton,
Véronique Gouverneur
Publication year - 2018
Publication title -
science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 12.556
H-Index - 1186
eISSN - 1095-9203
pISSN - 0036-8075
DOI - 10.1126/science.aar7941
Subject(s) - nucleophile , enantioselective synthesis , chemistry , catalysis , hydrogen bond , combinatorial chemistry , organocatalysis , organic chemistry , molecule
H-bond to deliver fluoride Simple fluoride salts are theoretically convenient reagents for carbon-fluorine bond formation. In practice, they are often insoluble in the solvents that dissolve their reaction partners. Pupoet al. developed urea-based catalysts that make fluoride soluble through hydrogen bonding. Moreover, their chiral substituents bias the reaction toward one of two mirror image products of C–F bond formation. This strategy should be applicable to the asymmetric addition of other salts, too.Science , this issue p.638
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