An efficient palladium-catalyzed N-alkylation of amines using primary and secondary alcohols

An efficient palladium-catalyzed N-alkylation of amines using primary and secondary alcohols

ACS Catalysis

10.1021/cs400799n

http://dx.doi.org/10.1021/cs400799n

Tuan Thanh Dang, Balamurugan Ramalingam, Abdul Majeed Seayad, Pei Shan Siah

10 October 2013

Dang, T. T.; Zhu, Y. H.; Ngiam, J. S. Y.; Ghosh, S. C.; Chen, A. Q.; Seayad, A. M., Palladium nanoparticles supported on ZIF-8 as an efficient heterogeneous catalyst for aminocarbonylation. ACS Catalysis 2013, 3, p 1406-1410.

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 °C under neat conditions. Interestingly, good to excellent yields were achieved when more challenging secondary alcohols were used as alkylating agents at 130–150 °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.

PublisherCopyrights

This work was funded by “GSK-EDB Singapore Partnership for Green and Sustainable Manufacturing and the Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), Singapore.

This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright©American Chemistry Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/cs400799n.

https://oar.a-star.edu.sg/communities-collections/articles/12720

2155-5435

Institute of Chemical and Engineering Sciences