The synthesis of pyrroles via acceptorless dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols mediated by a robust and reusable catalyst based on nanometer-sized iridium particles

Forberg, Daniel; Obenauf, Johannes; Friedrich, Martin; Hühne, Sven-Martin; Mader, W.; Motz, Günter; Kempe, Rhett

doi:10.1039/c4cy01018c

Cited by 89 publications

(67 citation statements)

References 76 publications

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“…(1), the reactions with 0.03 mol% of Pt/C for 96 h resulted in 83% yield, corresponding to TON of 2767. This TON is larger than those for previous homogeneous Ir (TON=1860) 4 and Ru (TON=150) 6 catalysts and a heterogeneous Ir catalyst (TON=260) 8 for the same reaction. Table 3 demonstrates substrate scope of the dehydrogenative synthesis of 2,5-disubstituted pyrroles from 1,2-amino alcohols (1) and 1.5 equiv.…”

Section: Resultsmentioning

confidence: 49%

“…The result shows that diglyme (entry 8) would serve as the best solvent. The reaction with various basic additives (entries 8,[14][15][16][17][18] showed that KOtBu (entry 8) was more effective than other bases such as K 2 CO 3 , Cs 2 CO 3 , NaOH, NaOMe and KOH.…”

Section: Resultsmentioning

confidence: 99%

“…This new method shows a good catalyst reusability and higher turnover number (TON) than previously-reported catalysts. 4,6,8 …”

Section: Introductionmentioning

confidence: 99%

“…Following the pioneering works, 3i,j several groups [4][5][6][7][8] have recently reported new synthetic protocols to get pyrroles from easily available starting materials. The protocols employ acceptorless dehydrogenative coupling methodology.…”

Section: Introductionmentioning

confidence: 99%

“…In this sense, Kempe's group developed a new heterogeneous catalyst, Ir@SiCN, that was effective for acceptorless dehydrogenative synthesis of pyrroles from 1,2-amino alcohols and secondary alcohols with KOtBu. 8 Although the heterogeneous system was successfully developed, the catalyst preparation could be complicated since they made a precursor by themselves and the preparation procedure requires several steps. Therefore, development of versatile heterogeneous catalytic systems is desired for easy access to this organic synthesis and its practical applications.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts

et al. 2016

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Direct synthesis of 2,5-disubstituted pyrroles has been achieved via acceptorless dehydrogenative heterocyclization of 1,2-aminoalcohols and secondary alcohols by utilizing a heterogeneous carbon-supported Pt catalyst (Pt/C). The optimized method gave 92 % yield of 2-ethyl-5-phenyl-1H-pyrrole as a desired product from 2-amino-1-butanol and 1-phenylethanol in the presence of 0.1 mol% of Pt/C and 1.1 equiv. of KOtBu. It has been revealed that Pt/C demonstrates superior catalytic activity to a number of catalysts tested in this study including other transition metal-loaded carbon and various metaloxide-supported Pt catalysts. In addition, turnover number (TON) obtained in the present system was found to be higher than those obtained in previously-reported catalytic systems. It is significant that the Pt/C catalyst could be recycled as a heterogeneous catalyst without significant loss in the activity and showed wide substrate scope for the 2,5-disubstituted pyrrole forming process.

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Section: Resultsmentioning

confidence: 49%

Section: Resultsmentioning

confidence: 99%

“…This new method shows a good catalyst reusability and higher turnover number (TON) than previously-reported catalysts. 4,6,8 …”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts

et al. 2016

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acceptorless dehydrogenative condensation

Boncli¹

2020

Catalysis From a to Z

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Iron Catalyzed Synthesis of Pyrimidines Under Air

et al. 2019

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Herein we report an iron-catalyzed multicomponent dehydrogenative functionalization of alcohols to pyrimidines under atmospheric conditions. Using a well-defined Fe(II)-complex featuring redox noninnocent 2-phenylazo-(1,10-phenanthroline) ligand, as a catalyst, a wide array of 2,4,6-trisubstituted pyrimidines were prepared via dehydrogenative coupling of primary and secondary alcohols with amidines under air at 100°C. A few control experiments were carried out to understand and unveil the plausible reaction mechanism.

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The synthesis of pyrroles via acceptorless dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols mediated by a robust and reusable catalyst based on nanometer-sized iridium particles

Abstract: The synthesis of pyrroles via acceptorless dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols mediated by a robust and reusable catalyst based on nanometer-sized iridium particles †

Cited by 89 publications

References 76 publications

Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts

Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts

acceptorless dehydrogenative condensation

Iron Catalyzed Synthesis of Pyrimidines Under Air

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