Efficient Ruthenium-Catalyzed N‑Methylation of Amines Using Methanol

An in situ-generated complex from [RuCp*Cl2]2 and dpePhos ligand is reported as an efficient catalyst in the presence of 5 mol % of LiOtBu for the N-methylation of amines using methanol as the methylating agent at moderate conditions, following hydrogen borrowing strategy. This simple catalyst syste...

Full description

Saved in:
Bibliographic Details
Published in:ACS catalysis 2015-07, Vol.5 (7), p.4082-4088
Main Authors: Dang, Tuan Thanh, Ramalingam, Balamurugan, Seayad, Abdul Majeed
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An in situ-generated complex from [RuCp*Cl2]2 and dpePhos ligand is reported as an efficient catalyst in the presence of 5 mol % of LiOtBu for the N-methylation of amines using methanol as the methylating agent at moderate conditions, following hydrogen borrowing strategy. This simple catalyst system provides selective N-monomethylation of substituted primary anilines and sulfonamides as well as N,N-dimethylation of primary aliphatic amines in excellent yields at 40–100 °C with good tolerance to reducible functional groups. The catalytic intermediate Cp*Ru­(dpePhos)­H was isolated and was shown to be active for methylation in the absence of base.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.5b00606