Abstract
(Equation Presented). The preparation of 3,3-disubstituted oxindoles by a formal C-H, Ar-H coupling of anilides is described. Highly efficient conditions have been identified using catalytic (5 mol %) Cu(OAc)2·H 2O with atmospheric oxygen as the reoxidant; no additional base is required, and the reaction can be run in toluene or mesitylene. Optimization studies are reported together with a scope and limitation investigation based on variation of the anilide precursors. The application of this methodology to prepare a key intermediate for the total synthesis of the anticancer, analgesic oxindole alkaloid Horsfiline is also described.
Original language | English (US) |
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Pages (from-to) | 3446-3449 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 12 |
Issue number | 15 |
DOIs | |
State | Published - Aug 6 2010 |
Externally published | Yes |