Either the C2‐ or the C3‐substituted product can be obtained with the same palladium(II) catalyst in an oxidative intermolecular alkenylation of indoles. A variety of conditions can be used for derivatization at the 3‐position; however, the presence of acetic acid is required for the C2‐selective process (see scheme). Further elaboration of the products by a similar CH functionalization process leads to the bisalkenylated indoles selectively.
Das C2‐ oder das C3‐substituierte Produkt kann bei der oxidativen intermolekularen Alkenylierung von Indolen mit dem gleichen Palladium(II)‐Katalysator erhalten werden. Eine Vielzahl an Bedingungen eignet sich für die Derivatisierung an der 3‐Position; dagegen erfordert der C2‐selektive Prozess Essigsäure (siehe Schema). Eine weitere ähnliche C‐H‐Funktionalisierung überführt die Produkte selektiv in die bisalkenylierten Indole.
Indole derivatives R 0140Palladium-Catalyzed Intermolecular Alkenylation of Indoles by Solvent-Controlled Regioselective C-H Functionalization. -A new general method for the selective intermolecular alkenylation of indoles is reported. In polar solvents, exclusively C3-functionalized products are obtained. In dioxane/AcOH functionalization at C-2 is favored. No reaction is observed for N-methylindole. -(GRIMSTER, N. P.; GAUNTLETT, C.; GODFREY, C. R. A.; GAUNT*, M. J.; Angew. Chem., Int. Ed. 44 (2005) 20, 3125-3129; Dep. Chem., Univ. Cambridge, Cambridge CB2 1EW, UK; Eng.) -S. Adam 38-123
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