Dearomatization reactions of N-heterocycles mediated by group 3 complexes.
Group 3 (Sc, Y, Lu, La) benzyl complexes supported by a ferrocene diamide ligand are reactive toward aromatic N-heterocycles by mediating their coupling and, in a few cases, the cleavage of their C-N bonds. When these complexes reacted with 2,2'-bipyridine or isoquinoline, they facilitated the alkyl migration of the benzyl ligand onto the pyridine ring, a process accompanied by the dearomatization of the N-heterocycle. The products of the alkyl-transfer reactions act as hydrogen donors in the presence of aromatic N-heterocycles, ketones, and azobenzene. Experimental and computational studies suggest that the hydrogen transfer takes place through a concerted mechanism. An interesting disproportionation reaction of the dearomatized, alkyl-substituted isoquinoline complexes is also reported.
Miller
Kevin L
KL
Department of Chemistry & Biochemistry, University of California, Los Angeles, California 90095, USA.
Williams
Bryan N
BN
Benitez
Diego
D
Carver
Colin T
CT
Ogilby
Kevin R
KR
Tkatchouk
Ekaterina
E
Goddard
William A
WA
Diaconescu
Paula L
PL