- Palladium-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines
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An efficient Pd(0)-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines is reported. Few methods have aimed to synthesize these scaffolds which are found in many natural products and have high bioactivity. This protocol features a robust c
- Zeidan, Nicolas,Bognar, Sabine,Lee, Sophia,Lautens, Mark
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supporting information
p. 5058 - 5061
(2017/11/07)
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- Carbopalladation of nitriles: Synthesis of 2,3-diarylindenones and polycyclic aromatic ketones by the Pd-catalyzed annulation of alkynes and bicyclic alkenes by 2-iodoarenenitriles
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2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(O)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon-nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.
- Pletnev, Alexandre A.,Tian, Qingping,Larock, Richard C.
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p. 9276 - 9287
(2007/10/03)
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- 2-(Tosylamino)benzyltrimethylammonium halides as precursors of 2-substituted indoles
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The reactions of 2-(tosylamino)benzyltrimethylammonium halides (1) with dimethylsulfonium 2-oxo-2-phenylethylide (6b), dimethylsulfonium 2-ethoxy-2-oxo-ethylide (6c) and dimethylsulfonium cyanomethylide (6d) are useful synthetic routes to 2-substituted indoles (8b-d). The relationship between reaction conditions and selectivity is discussed.
- Croce, Piero Dalla,Ferraccioli, Raffaella,La Rosa, Concetta
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p. 2397 - 2407
(2007/10/03)
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- INTRODUCTION OF NUCLEOPHILES OR ETHYL GROUP TO THE INDOLE NUCLEUS THROUGH NUCLEOPHILIC SUBSTITUTION AND/OR RADICAL REACTIONS OF 1-METHOXYINDOLE-3- AND -2-CARBOXALDEHYDE
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1-Methoxyindole-3- and -2-carboxaldehyde were found to undergo nucleophilic substitution and radical reactions resulting in the introduction of nucleophiles and/or ethyl group at the 2- or 3-position.
- Yamada, Fumio,Fukui, Yoshikazu,Shinmyo, Daisuke,Somei, Masanori
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