The catalytic hydrogenation of indoles

Smith, Amy C.; Utley, James H. P.

doi:10.1039/c19650000427

Cited by 7 publications

(6 citation statements)

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“…These include, with varying degrees of certitude, 9-substituted anthracenes, where the 10,10 0 -r-dimer is found for 9-methoxycarbonyl- [16], 9-nitro- [17,18], 9-cyano- [19] and 9-acetylanthracene [20]. Similarly, dimerization at the site of highest spin density is seen with 1,3,5-tricyanobenzene [21,22], dimerization at the 2-position.…”

Section: Correlation Of K Dim With Spin Densitymentioning

confidence: 84%

Reversible dimerization of the anion radicals of some dicyanonaphthalenes

Sánchez

Evans

2011

Journal of Electroanalytical Chemistry

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Section: Correlation Of K Dim With Spin Densitymentioning

confidence: 84%

Reversible dimerization of the anion radicals of some dicyanonaphthalenes

Sánchez

Evans

2011

Journal of Electroanalytical Chemistry

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“…The beneficial effect of the protic acid on the hydrogenation rate is not surprising, as also the heterogeneous hydrogenation of IN with either Raney nickel or copper chromate requires the presence of strong acids to occur …”

Section: Resultsmentioning

confidence: 99%

Hydrogenation of Indole by Phosphine-Modified Rhodium and Ruthenium Catalysts

et al. 2002

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The selective hydrogenation of indole (IN) to indoline (INE) by rhodium and ruthenium catalysts modified with the tripodal polyphosphine ligand MeC(CH 2 PPh 2 ) 3 (triphos) has been investigated in the homogeneous phase. Both [Rh(DMAD)(triphos)]PF 6 (DMAD ) dimethyl acetylenedicarboxylate) and [Ru(MeCN) 3 (triphos)](SO 3 CF 3 ) 2 have been found to generate effective catalysts for the conversion of IN to INE in THF in the presence of triflic acid. The protic acid is required to generate the 3H-indolium cation, which contains a localized CdN bond. The rhodium precursor was more efficient than the ruthenium species and allowed for hydrogenation of the substrate even at 60 °C with turnover frequencies as high as 100. Catalytic experiments in autoclaves and in high-pressure sapphire NMR tubes have provided valuable information on the hydrogenation mechanism of IN.

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“…Addition of ammonium formate did not improve the reaction. Attempts to reduce either 84 or 87 to the corresponding indolines (HBF 4 (aq)/PtO 2 /20 °C) were also unsuccessful. Murakami et al …”

Section: Resultsmentioning

confidence: 99%

The Synthesis of η²-β-Vinylpyrrole Complexes and Their Conversion to Highly Substituted Indoles

et al. 1996

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A series of 4,5-η 2 -Os(II)pentaammine-3-vinylpyrrole complexes are synthesized from the corresponding 1-methylpyrrole complex by an electrophilic addition at the β-carbon, C(3), of the pyrrole ring. Four independent synthetic routes to β-vinylpyrrole complexes are described, each introducing different functionality on the pendant double bond. The uncoordinated portion of these complexes chemically and structurally resembles an aminodiene and as such readily undergoes Diels-Alder reactions with suitably activated dienophiles to generate the 5,6,7,7atetrahydroindole nucleus. These tetrahydroindole complexes can be decomplexed and oxidized with DDQ to generate a series of highly functionalized indoles.

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The catalytic hydrogenation of indoles

Cited by 7 publications

References 0 publications

Reversible dimerization of the anion radicals of some dicyanonaphthalenes

Reversible dimerization of the anion radicals of some dicyanonaphthalenes

Hydrogenation of Indole by Phosphine-Modified Rhodium and Ruthenium Catalysts

The Synthesis of η²-β-Vinylpyrrole Complexes and Their Conversion to Highly Substituted Indoles

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The catalytic hydrogenation of indoles

Cited by 7 publications

References 0 publications

Reversible dimerization of the anion radicals of some dicyanonaphthalenes

Reversible dimerization of the anion radicals of some dicyanonaphthalenes

Hydrogenation of Indole by Phosphine-Modified Rhodium and Ruthenium Catalysts

The Synthesis of η2-β-Vinylpyrrole Complexes and Their Conversion to Highly Substituted Indoles

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The Synthesis of η²-β-Vinylpyrrole Complexes and Their Conversion to Highly Substituted Indoles