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Development of Decarboxylative Coupling Processes for the Synthesis of Azomethines and Ketones
Author(s) -
Collet Florence,
Song Bingrui,
Rudolphi Felix,
Gooßen Lukas J.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101103
Subject(s) - chemistry , aryl , halide , decarboxylation , ketone , catalysis , bimetallic strip , organic chemistry , coupling reaction , combinatorial chemistry , alkyl
A bimetallic catalyst system has been developed that allows the synthesis of azomethines by a one‐pot three‐component decarboxylative coupling, starting from simple, nontoxic precursors, i.e. potassium α‐oxo carboxylates, aryl halides and primary amines. In the presence of 15 mol‐% copper/phenanthroline and 1 mol‐% Pd/dppf, a wide range of valuable imines is conveniently accessible in high yields at 100 °C, an unprecedentedly low temperature for redox‐neutral decarboxylative cross‐coupling reactions. Hydrogenation of the azomethine products leads to secondary amines. Alternatively, they can be hydrolyzed in situ to aryl ketones. The resulting ketone synthesis via azomethine intermediates is also of interest as it gives higher yields at much lower temperatures than the direct decarboxylative coupling of α‐oxo carboxylates with aryl halides.