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Merging C−H Activation and Alkene Difunctionalization at Room Temperature: A Palladium-Catalyzed Divergent Synthesis of Indoles and Indolines
EPrints@IICB
View Archive Info| Field | Value | |
| Title |
Merging C−H Activation and Alkene Difunctionalization at Room Temperature: A Palladium-Catalyzed Divergent Synthesis of Indoles and Indolines
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| Creator |
Manna, Manash Kumar
Hossian, Asik Jana, Ranjan |
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| Subject |
Chemistry
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| Description |
A palladium-catalyzed 1,2-carboamination through C−H activation at room temperature is reported for the synthesis of 2-arylindoles, and indolines from readily available, inexpensive aryl ureas and vinyl arenes. The reaction initiates with a urea-directed electrophilic ortho palladation, alkene insertion, and β-hydride elimination sequences to provide the Fujiwara−Moritani arylation product. Subsequently, aza-Wacker cyclization, and β-hydride elimination provide the 2-arylindoles in high yields. Intercepting the common σ-alkyl-Pd intermediate, corresponding indolines are also achieved. The indoline formation is attributed to the generation of stabilized, cationic π-benzyl-Pd species to suppress β-hydride elimination. |
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| Publisher |
American Chemical Society
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| Date |
2015
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/2247/1/ORGANIC_LETTERS__Volume_17(_3_)_672%2D675_2015[57].pdf
Manna, Manash Kumar and Hossian, Asik and Jana, Ranjan (2015) Merging C−H Activation and Alkene Difunctionalization at Room Temperature: A Palladium-Catalyzed Divergent Synthesis of Indoles and Indolines. Organic Letters, 17 (3). pp. 672-675. |
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| Relation |
http://dx.doi.org/10.1021/ol5036968
http://www.eprints.iicb.res.in/2247/ |
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