sp(3) C-H Bond Activation with Ruthenium(II) Catalysts and C(3)-Alkylation of Cyclic Amines

A selective C(3)-alkylation via activation/functionalization of sp(3) C-H bond of saturated cyclic amines was promoted by (arene)ruthenium(II) complexes featuring a bidentate phosphino-sulfonate ligand upon reaction with aldehydes. This highly regioselective sustainable transformation takes place vi...

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Published inJournal of the American Chemical Society Vol. 133; no. 27; pp. 10340 - 10343
Main Authors Sundararaju, Basker, Achard, Mathieu, Sharma, Gangavaram V. M., Bruneau, Christian
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 13.07.2011
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALKENES
DEHYDROGENATION
HYDROGEN-TRANSFER REACTIONS
TERTIARY-AMINES
BORROWING HYDROGEN
SODIUM-CYANIDE
NITROGEN ATOM
COMPLEXES
ADJACENT
OXIDATIVE CYANATION
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Summary:A selective C(3)-alkylation via activation/functionalization of sp(3) C-H bond of saturated cyclic amines was promoted by (arene)ruthenium(II) complexes featuring a bidentate phosphino-sulfonate ligand upon reaction with aldehydes. This highly regioselective sustainable transformation takes place via initial dehydrogenation of cyclic amines and hydrogen autotransfer processes.
ISSN:0002-7863
DOI:10.1021/ja203875d