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Expedient Trimethylaluminium‐Promoted One‐Pot Synthesis of Functional Heteroaromatic and Carbocyclic Trifluoroethylamines
Author(s) -
Allendörfer Nadine,
Sudau Alexander,
Bräse Stefan
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000188
Subject(s) - chemistry , trifluoromethyl , borane , combinatorial chemistry , organic chemistry , sulfide , amide , one pot synthesis , ketone , derivative (finance) , organocatalysis , enantioselective synthesis , catalysis , alkyl , financial economics , economics
Abstract The synthesis of trifluoroethylamines as amide bond mimics is an interesting topic in current research. They are well known tools in pharmaceutical and agrochemical industry. Other methods described in literature are often restricted to few substrates. We herein report a new synthetic approach towards this class of substances. First, the trimethylaluminium‐promoted generation of a trifluoromethyl‐ketimine from the corresponding trifluoromethyl ketone and an aniline derivative was investigated. Next, the ketimine was converted into the trifluoroethylamines in a one‐pot reaction by simple addition of borane‐methyl sulfide complex.