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Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O‐, S‐, and N‐Nucleophiles
Author(s) -
Gellert Beate A.,
Kahlcke Nils,
Feurer Markus,
Roth Stefanie
Publication year - 2011
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.201101819
Subject(s) - triflic acid , nucleophile , chemistry , catalysis , organic chemistry , coupling reaction , ketone , combinatorial chemistry
Highly efficient metal‐free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1–5 mol %) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.