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Palladium-Catalyzed Functionalization of Indoles with 2-Acetoxymethyl-Substituted Electron-Deficient Alkenes.
- Source :
-
Journal of Organic Chemistry . 12/22/2006, Vol. 71 Issue 26, p9865-9868. 4p. 4 Charts. - Publication Year :
- 2006
-
Abstract
- New functionalizations of indoles via palladium-catalyzed reaction of indoles and 2-acetoxymethyl-substituted electron-deficient alkenes are reported. It was found that for N-protected indoles the reaction proceeded smoothly in the presence of 5 mol % of Pd(acac)2 and 10 mol % of PPh3 at 80 °C in HOAc, while for N-unprotected indoles, the reaction was carried out by using 5 mol % of Pd(dba)2 or 2.5 mol % of Pd2(dba)3•CHCI3 with 10 mol % of 2,2′-bipyridine as the catalyst in toluene. This strategy allows the selective installation of electron-deficient olefin functionality at the 3-position of indoles, which might be difficult to obtain by other methods and can be further elaborated. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 71
- Issue :
- 26
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 23593541
- Full Text :
- https://doi.org/10.1021/jo061546s