- Palladium-catalyzed regiocontrolled internal heteroarylation of electron-rich olefins with heteroaryl halides
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A highly efficient palladium-catalyzed Heck coupling reaction of heteroaryl halides with electron-rich vinyl ether and hydroxyalkyl vinyl ethers is described. It was found that the choice of solvent, ligand, and reaction temperature had a fundamental influence on the regioselectivity and reactivity of the reaction, and the combination of Pd(OAc)2 and DPPF in ethylene glycol led to the most effective catalytic system. Under these conditions, a variety of heteroaryl halides reacted very quickly with electron-rich olefins to afford exclusively the branched products in good to excellent yields without employing triflates, halide scavengers, or ionic liquids.
- Xu, Dan,Liu, Zhihua,Tang, Weijun,Xu, Lijin,Hyder, Zeynab,Xiao, Jianliang
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p. 6104 - 6107
(2009/04/04)
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- Syntheses of acetylquinolines and acetylisoquinolines via palladium-catalyzed coupling reactions
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Acetylquinolines and acetylisoquinolines were obtained from the corresponding chloro-, bromo- or trifluoromethylsulfonyloxy-heteroaromatics via four different palladium-catalyzed coupling reactions: (i) Stille coupling with tri(n-butyl)-1-ethoxyvinylstannane; (ii) Negishi coupling with 1-ethoxyvinylzinc chloride; (iii) cross-coupling with tri(1-ethoxyvinyl)indium; (iv) Heck arylation of n-butyl vinyl ether.
- Legros, Jean-Yves,Primault, Ga?lle,Fiaud, Jean-Claude
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p. 2507 - 2514
(2007/10/03)
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- Cyclising Nucleophilic Addition to Azinium Systems. Part 1. Reaction of 3-Indol-2-ylpyridine, 3-Indol-2-ylquinoline, 4-Indol-2-ylisoquinoline and Pyridocarbazoles with Acetic Anhydride
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Two pyridocarbazoles were shown to react smoothly with acetic anhydride to give 1-acetyl-1,12a-dihydronaphthyridinocarbazol-11(12H)-ones. 3-Indol-2-ylquinoline and 3-indol-2-ylpyridine reacted in an analogous fashion though with further complications in the latter case. 4-Indol-2-ylisoquinoline gave E-2-acetyl-1-(1-acetylindol-2-ylmethylene)-2,3-dihydro-3-(2-oxopropyl)-1H-isoindole, the structure of which was determined by a detailed study of its (1)H n.m.r. spectrum with decoupling, n.O.e. and relaxation time measurements.
- Baradarani, M. Mehdi,Dalton, Lesley,Heatley, Frank,Cohylakis, Demetrios,Joule, John A.
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p. 1503 - 1508
(2007/10/02)
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