Lewis Acid Catalyzed Benzylic C–H Bond Functionalization of Azaarenes; Addition to Imines and Enones

Abstract Lewis acid catalyzed benzylic C–H bond functionalization of alkyl-substituted azaarenes is described. The addition to N -tosyl imines proceeded under solvent-free conditions using various Lewis acids. Cu(OTf) 2 was the best Lewis acid, and 1,2-addition proceeded at 60–120 °C, giving product...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2012-07, Vol.44 (14), p.2185-2194
Main Authors: Komai, Hirotomo, Yoshino, Tatsuhiko, Matsunaga, Shigeki, Kanai, Motomu
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
special topic
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Summary:Abstract Lewis acid catalyzed benzylic C–H bond functionalization of alkyl-substituted azaarenes is described. The addition to N -tosyl imines proceeded under solvent-free conditions using various Lewis acids. Cu(OTf) 2 was the best Lewis acid, and 1,2-addition proceeded at 60–120 °C, giving products in 23–92% yield. On the other hand, strongly Lewis acidic rare-earth metal triflates, Sc(OTf) 3 and Y(OTf) 3 , were essential to promote the 1,4-addition of alkyl-substituted azaarenes to enones, and products were obtained in 60–96% yield.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0031-1291041