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2 arylated product, but not a 3,3-disubstituted indole. The presumed mechanism follows: initial deprotonation of indole, followed by arylation at C-3, and finally retro-Mannich to give the observed product. This work does not represent the first example of the direct arylation of an indole to give a C-3 quaternary center, rather, it was the 'presumed' intermediate that served as precedent for the reaction of bis-aryl iodide salts with indole derivatives. Our work is first to isolate and characterize C-3 quaternary indolines prepared by reaction of an indole and a bis-aryl iodide.
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2 arylated product, but not a 3,3-disubstituted indole. The presumed mechanism follows: initial deprotonation of indole, followed by arylation at C-3, and finally retro-Mannich to give the observed product. This work does not represent the first example of the direct arylation of an indole to give a C-3 quaternary center, rather, it was the 'presumed' intermediate that served as precedent for the reaction of bis-aryl iodide salts with indole derivatives. Our work is first to isolate and characterize C-3 quaternary indolines prepared by reaction of an indole and a bis-aryl iodide. Ebnöther A., Niklaus P., and Süess R. Helv. Chim. Acta (1969) 629-638
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0011668108
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When unavailable commercially, bisacetoxy aryl iodides were prepared in one step according to Skulski's protocol: All boronic acids used are commercially available
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When unavailable commercially, bisacetoxy aryl iodides were prepared in one step according to Skulski's protocol:. Kazmierczak P., Skulski L., and Kraszkiewicz L. Molecules 6 (2001) 881-891 All boronic acids used are commercially available
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39
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62049083902
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note
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As it pertains to the conversion from skatole to the unstable indolenine.
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40
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62049083738
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note
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3-iodane.
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41
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62049085396
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note
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Reduction to the indoline is aided by the addition of silica gel.
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