Palladium-Catalyzed Methylation of Nitroarenes with Methanol

Angewandte Chemie
Lin WangMatthias Beller

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]-1H-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.

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Citations

Jul 22, 2020·Chemical Communications : Chem Comm·Ni ShenJun-An Ma
Mar 7, 2020·Organic & Biomolecular Chemistry·Bhaskar PaulSabuj Kundu
May 26, 2021·The Journal of Organic Chemistry·Siba P MidyaEkambaram Balaraman
Oct 9, 2019·The Journal of Organic Chemistry·Shao-Peng WangJun-An Ma
Nov 9, 2019·The Journal of Organic Chemistry·Vishakha GoyalKishore Natte
Jul 25, 2019·The Journal of Organic Chemistry·Ramesh MamidalaKrishnan Venkatasubbaiah
Apr 8, 2020·The Journal of Organic Chemistry·Yevgen M PoronikDaniel T Gryko

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