Journal
ACS CATALYSIS
Volume 3, Issue 11, Pages 2536-2540Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs400799n
Keywords
alkylation; alcohol activation; hydrogen borrowing; palladium catalyst; amine synthesis
Categories
Funding
- GSK-EDB Singapore Partnership for Green and Sustainable Manufacturing
- Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), Singapore
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PdCl2 in the presence of dppe or Xantphos(t-Bu) as the ligand is found to be an efficient catalyst for the N-alkylation of various primary and cyclic secondary amines using primary alcohols at 90-130 degrees C under neat conditions. Interestingly, good to excellent yields were achieved when more challenging secondary alcohols were used as alkylating agents at 130-150 degrees C. The reaction could be easily scaled up, as demonstrated for a 10 mmol scale achieving yields up to 90% with a TON of 900.
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