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Catalyst and base controlled site-selective sp2 and sp3 direct arylation of azine N-oxides
- Source :
-
Tetrahedron . Apr2009, Vol. 65 Issue 16, p3155-3164. 10p. - Publication Year :
- 2009
-
Abstract
- Abstract: Site-selective direct arylation of both sp2 and sp3 sites on azine N-oxide substrates is described. The arylation reactions are carried out in either a divergent manner or a sequential manner. The sp3 arylation reaction is applied to the synthesis of the natural products, papaverine and crykonisine, and a rationale for low reactivity of electron-deficient aryl halides is provided. Mechanistic investigations point toward the intimate involvement of the base in the mechanism of these reactions. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 65
- Issue :
- 16
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 37157603
- Full Text :
- https://doi.org/10.1016/j.tet.2008.12.004