10.1021/acscatal.6b03088.s001
Jeff Joseph
A. Celaje
Jeff Joseph
A.
Celaje
Xingyue Zhang
Xingyue
Zhang
Forrest Zhang
Forrest
Zhang
Lisa Kam
Lisa
Kam
Jessica R. Herron
Jessica R.
Herron
Travis J. Williams
Travis J.
Williams
A Base and Solvent-Free Ruthenium-Catalyzed Alkylation
of Amines
American Chemical Society
2016
conditions offer
reaction conditions
Mechanistic studies
hydrogen-borrowing mechanism
group compatibility
Solvent-Free Ruthenium-Catalyzed Alkylation
imine formation
redox steps
chemoselective benzylic N-alkylation
catalyst
2016-12-30 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/A_Base_and_Solvent-Free_Ruthenium-Catalyzed_Alkylation_of_Amines/4531763
A (pyridyl)phosphine-ligated
ruthenium(II) catalyst is reported
for the chemoselective benzylic N-alkylation of amines, via a hydrogen-borrowing
mechanism. The catalyst operates under mild conditions, neat, and
without a base or other additive. These conditions offer remarkable
functional group compatibility for applications in organic synthesis,
including reactions involving phenols and anilines, which are very
difficult to achieve. Mechanistic studies suggest that, unlike other
catalysts for this reaction, the redox steps are fast and reversible
while imine formation is slow. We perceive that this is the origin
of the selectivity realized with these reaction conditions.