Synthesis of a 1,3,4,5-tetrahydrobenz[cd]indole via the Vicarious Nucleophilic substitution of hydrogen

Ma̧jkosza, Mieczysa̵w; Stalewski, Jacek; Wojciechowski, Krzysztof; Danikiewicz, Witold

doi:10.1016/s0040-4020(96)00963-5

Cited by 18 publications

(9 citation statements)

References 30 publications

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“…19 Scheme 4 shows a comparative study of the performance of catalysts 1b, 1c, 6b, and 7b in CM of phenyl vinyl sulfone and the highly substituted indole 29. Although CM of this challenging substrate, a "dead-end intermediate" 20 in total synthesis of 1,3,4,5-tetrahydrobenz[c,d]indol-4-amine alkaloids, 21 is possible with Grubbs's "second-generation" carbene 1b, the highest conversions and lowest catalyst loadings can be achieved in the case of 6b and 7b (Scheme 4). The catalytic CM of selected R,β-unsaturated substrates was then examined.…”

Section: Relative Reactivity Of Various Ruthenium Catalystsmentioning

confidence: 99%

Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation

et al. 2004

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The design, synthesis, stability, and catalytic activity of nitro-substituted Hoveyda-Grubbs metathesis catalysts are described. The highly active and stable meta- and para-substituted complexes are attractive from a practical point of view. These catalysts operate in very mild conditions and can be successfully applied in various types of metathesis [ring-closing metathesis, cross-metathesis (CM), and enyne metathesis]. Although the presence of a NO(2) group leads to catalysts that are dramatically more active than both the second-generation Grubbs's catalyst and the phosphine-free Hoveyda's carbene, enhancement of reactivity is somewhat lower than that observed for a sterically activated Hoveyda-Grubbs catalyst. Attempts to combine two modes of activation, steric and electronic, result in severely decreasing a catalyst's stability. The present findings illustrate that different Ru catalysts turned out to be optimal for different applications. Whereas phosphine-free carbenes are catalysts of choice for CM of various electron-deficient substrates, they exhibit lower reactivity in the formation of tetrasubstituted double bonds. This demonstrates that no single catalyst outperforms all others in all possible applications.

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Section: Relative Reactivity Of Various Ruthenium Catalystsmentioning

confidence: 99%

Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation

et al. 2004

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“…136, 137 The reaction is very general and has been exploited by Makosza and co-workers in a synthesis of 5-allyloxy-3-(4-tolylsulfonyl)-1H-indole for use in 1,3,4,5-tetrahydrobenzo[cd]indole studies. 138 The requisite isocyanide precursor was synthesized by a vicarious nucleophilic substitution (VNS) reaction as developed by Makosza. 139, 140 The elegant free-radical cyclization version of the Saegusa indole synthesis as developed by Fukuyama is presented in Section 7.1.…”

Section: Saegusa Indole Synthesismentioning

confidence: 99%

Recent developments in indole ring synthesis—methodology and applications

Gribble

2000

J. Chem. Soc., Perkin Trans. 1

958

294

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Section: Relative Reactivity Of Various Ruthenium Catalystsmentioning

confidence: 99%

Nitro‐Substituted Hoveyda—Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity Through Electronic Activation.

et al. 2004

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Abstract:The design, synthesis, stability, and catalytic activity of nitro-substituted Hoveyda-Grubbs metathesis catalysts are described. The highly active and stable meta-and para-substituted complexes are attractive from a practical point of view. These catalysts operate in very mild conditions and can be successfully applied in various types of metathesis [ring-closing metathesis, cross-metathesis (CM), and enyne metathesis]. Although the presence of a NO2 group leads to catalysts that are dramatically more active than both the second-generation Grubbs's catalyst and the phosphine-free Hoveyda's carbene, enhancement of reactivity is somewhat lower than that observed for a sterically activated Hoveyda-Grubbs catalyst. Attempts to combine two modes of activation, steric and electronic, result in severely decreasing a catalyst's stability. The present findings illustrate that different Ru catalysts turned out to be optimal for different applications. Whereas phosphine-free carbenes are catalysts of choice for CM of various electrondeficient substrates, they exhibit lower reactivity in the formation of tetrasubstituted double bonds. This demonstrates that no single catalyst outperforms all others in all possible applications.

show abstract

Synthesis of a 1,3,4,5-tetrahydrobenz[cd]indole via the Vicarious Nucleophilic substitution of hydrogen

Cited by 18 publications

References 30 publications

Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation

Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation

Recent developments in indole ring synthesis—methodology and applications

Nitro‐Substituted Hoveyda—Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity Through Electronic Activation.

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