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  • Title: Easy access to isoquinolines and tetrahydroquinolines from ketoximes and alkynes via rhodium-catalyzed C-H bond activation.
    Author: Parthasarathy K, Cheng CH.
    Journal: J Org Chem; 2009 Dec 18; 74(24):9359-64. PubMed ID: 19894732.
    Abstract:
    Described herein is a convenient and highly regioselective synthesis of substituted isoquinoline derivatives from various aromatic ketoximes and alkynes via a one-pot, rhodium-catalyzed C-H bond activation. In addition, tetrahydroquinoline derivatives are formed in good yields from 2-arylidene-1-cyclohexanone oximes possessing an exocyclic double bond and from tetrahydroxanthone oximes. A possible mechanism is proposed that involves chelation-assisted C-H activation via oxidative addition of Rh(I) to an ortho-C-H bond, insertion of the alkyne, reductive elimination, intramolecular electrocyclization, and aromatization. This mechanism is supported by isolation of the ortho-alkenylation products 7p and 7q. Also described herein is an example of an iridium-catalyzed activation of an sp(3) C-H bond.
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