Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (-)-rhazinilam and its analogues
(2001) Canadian Journal of Chemistry — Vol. 79, n° 11, p. 1827-1839 (2001)
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- Abstract
- Suzuki cross-coupling reactions of 3-pyrroleboronic acid derivatives with haloaromatics and the reverse process i.e., the coupling of 3-iodo(bromo)pyrroles with arylboronic acids have been investigated as a potential key step in the synthesis of (-)-rhazinilam and analogues. It was found that 3-iodo-2-formyl-1-tosylpyrroles efficiently coupled with a variety of arylboronic acids in the presence of PdCl2(dppf) as catalyst. This catalytic system is compatible with a broad spectrum of arylboronic acids - electron-rich, electron-poor, hindered, heterocyclic - which easily coupled with the pyrrole substrate.
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Ghosez, L., Franc, C., Denonne, F., Cuisinier, C., & Touillaux, R. (2001). Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (-)-rhazinilam and its analogues. Canadian Journal of Chemistry, 79(11), 1827-1839. https://doi.org/10.1139/cjc-79-11-1827 (Original work published 2001)