TY - JOUR

T1 - Dehydrogenative Synthesis of Imines from Alcohols and Amines Catalyzed by a Ruthenium N-Heterocyclic Carbene Complex

A1 - Maggi,Agnese

A1 - Madsen,Robert

AU - Maggi,Agnese

AU - Madsen,Robert

PB - American Chemical Society

PY - 2012

Y1 - 2012

N2 - <p>A new method for the direct synthesis of imines from alcohols and amines is described where hydrogen gas is liberated. The reaction is catalyzed by the ruthenium N-heterocyclic carbene complex [RuCl₂(IiPr)(p-cymene)] in the presence of the ligand DABCO and molecular sieves. The imination can be applied to a variety of primary alcohols and amines and can be combined with a subsequent addition reaction. A deuterium labeling experiment indicates that the catalytically active species is a ruthenium dihydride. The reaction is believed to proceed by initial dehydrogenation of the alcohol to the aldehyde, which stays coordinated to ruthenium. Nucleophilic attack of the amine affords the hemiaminal, which is released from ruthenium and converted into the imine.</p>

AB - <p>A new method for the direct synthesis of imines from alcohols and amines is described where hydrogen gas is liberated. The reaction is catalyzed by the ruthenium N-heterocyclic carbene complex [RuCl₂(IiPr)(p-cymene)] in the presence of the ligand DABCO and molecular sieves. The imination can be applied to a variety of primary alcohols and amines and can be combined with a subsequent addition reaction. A deuterium labeling experiment indicates that the catalytically active species is a ruthenium dihydride. The reaction is believed to proceed by initial dehydrogenation of the alcohol to the aldehyde, which stays coordinated to ruthenium. Nucleophilic attack of the amine affords the hemiaminal, which is released from ruthenium and converted into the imine.</p>

UR - http://pubs.acs.org/doi/abs/10.1021/om201095m

U2 - 10.1021/om201095m

DO - 10.1021/om201095m

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 1

VL - 31

SP - 451

EP - 455

ER -