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Palladium‐Catalyzed Methylation of Nitroarenes with Methanol
Author(s) -
Wang Lin,
Neumann Helfried,
Beller Matthias
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814146
Subject(s) - chemistry , palladium , catalysis , methanol , imidazole , isopropyl , combinatorial chemistry , organic chemistry , ligand (biochemistry) , methylation , receptor , biochemistry , gene
Abstract A procedure for the synthesis of N ‐methyl‐arylamines directly from nitroarenes using methanol as green methylating agent was developed. The key to success is the use of a specific catalyst system consisting of palladium acetate and the ligand 1‐[2,6‐bis(isopropyl)phenyl]‐2‐[tert‐butyl(2‐pyridinyl)phosphino]‐1 H ‐Imidazole ( L1 ). The generality of this protocol is demonstrated in the synthesis of more than 20 N ‐methyl‐arylamines under comparably mild conditions. Combining this novel methodology with subsequent coupling processes using the same catalyst allows for efficient diversification of aromatic nitro compounds to a broad variety of amines including drug molecules.