Cycloisomerization of 2‐Alkynylanilines to Indoles Catalyzed by Carbon‐Supported Gold Nanoparticles and Subsequent Homocoupling to 3,3′‐Biindoles

Perea‐Buceta, Jesus E.; Wirtanen, Tom; Laukkanen, Otto-Ville; Mäkelä, Mikko; Nieger, Martin; Melchionna, Michele; Huittinen, Nina; López-Sánchez, José Antonio; Helaja, Juho

doi:10.1002/anie.201305579

Cited by 103 publications

(54 citation statements)

References 67 publications

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“…In connection with our previous reports on the cyclization reaction of 2‐alkynylanilines to indoles by homogeneous cationic Au III catalysis19 and heterogeneous Au/C catalysis,20 we envisaged that a similar Au‐catalyzed approach could be applied to the synthesis of 4‐quinolones by using 2‐acetylic ketones of anilines as precursors (Scheme ). Further support to our hypothesis is provided by some recent reports on hydroamination reactions catalyzed by gold species.…”

Section: Introductionmentioning

confidence: 94%

On the Nature of Interactions between Ionic Liquids and Small Amino‐Acid‐Based Biomolecules

et al. 2013

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During the last decade, ionic liquids (ILs) have revealed promising properties and applications in many research fields, including biotechnology and biological sciences. The focus of this contribution is to give a critical review of the phenomena observed and current knowledge of the interactions occurring on a molecular basis. As opposed to the huge advances made in understanding the properties of proteins in ILs, complementary investigations dealing with interactions between ILs and peptides or oligopeptides are underrepresented and are mostly only of phenomenological nature. However, the field has received more attention in the last few years. This Review features a meta-analysis of the available data and findings and should, therefore, provide a basis for a scientifically profound understanding of the nature and mechanisms of interactions between ILs and structured or nonstructured peptides. Fundamental aspects of the interactions between different peptides/oligopeptides and ILs are complemented by sections on the experimental (spectroscopy, structural biology) and theoretical (computational chemistry) possibilities to explain the phenomena reported so far in the literature. In effect, this should lead to the development of novel applications and support the understanding of IL-solute interactions in general.

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Section: Introductionmentioning

confidence: 94%

On the Nature of Interactions between Ionic Liquids and Small Amino‐Acid‐Based Biomolecules

et al. 2013

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“…[7] Such ar eaction, however, often gives ac omplicated mixture of oligomers,a nd the desired product is obtained in low to moderate yields.Recently,Pd-catalyzed cyclodimerization of biphenyl derivatives based on Suzuki-Miyaura coupling [8] and Ullman-type coupling [9] (Scheme 1b and c) has emerged as an effective tool for preparing tetraphenylenes.S hi et al [10] and Zhang et al [11] independently developed an ovel reaction system involving the catalytic CÀHf unctionalization [12] of 2iodo-1,1'-biphenyl derivatives (Scheme 1d). [14] Despite the significant research interest in this field, there have been limited achievements [15] to date in the efficient construction of heteroarene-fused COTs besides those represented in Scheme 1a. [13] Furthermore,a ne legant study on the Rhcatalyzed enantioselective [2+ +2+ +2] cycloaddition of triynes has been reported by Shibata and co-workers.…”

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confidence: 99%

Palladium‐Catalyzed Synthesis of Heteroarene‐Fused Cyclooctatetraenes through Dehydrogenative Cyclodimerization

2017

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Arene-fused cyclooctatetraenes (COTs) possess unique structural and electronic properties that originate from their saddle-shaped π-conjugated architectures. Considerable attention has been paid to the transition-metal-mediated synthesis of these cyclic compounds; however, there have been limited achievements to date in the efficient construction of heteroarene-fused COTs. In this contribution, we report a novel Pd-catalyzed dehydrogenative cyclodimerization of biheteroarenes through four-fold C-H activation toward the synthesis of a series of heteroarene-fused COTs. A set of mechanistic investigations indicated the involvement of high-valent Pd species prior to the dimerization event in the catalytic cycle. The redox behavior of the obtained COTs is also described briefly.

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“…The appropriate solvent and amount were determined for the effective catalysis.T he reaction could take place either toluene or methanol ( Table 1, entries 1-3). Ther eaction did not proceed in the presence of UiO-67-BPY alone (Table S1, entries [11][12][13][14][15][16][17][18] or Zn(BF 4 ) 2 ·x H 2 Oa lone (entries 27 and 28). Unsurprisingly,w ith lower amounts of Zn-UiO-67-BPY,t he yield decreased (entries 6-10).…”

Section: Zuschriftenmentioning

confidence: 99%

A Reusable MOF‐Supported Single‐Site Zinc(II) Catalyst for Efficient Intramolecular Hydroamination of o‐Alkynylanilines

Zhou

et al. 2019

Angewandte Chemie

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The exploitation of new and active earth-abundant metal catalysts is critical for sustainable chemicalp roduction. Herein, we demonstrate the design of highly efficient, robust, and reusable Zn II -bipyridine-based metal-organic framework (MOF) catalysts for the intramolecular hydroamination of oalkynylanilines to indoles.U nder similar conditions homogeneous catalytic systems mainly provide hydrolysate.O ur results prove that MOFs support unique internal environments that can affect the direction of chemical reactions.T he Zn IIcatalyzedh ydroamination reaction can be conducted without additional ligands,b ase,o ra cid, and is thus av ery clean reaction system with regardtoi ts environmental impact. Scheme 1. a) Previous hydroamination methods and b) the proposed MOF-supported single-site zinc catalyst for the intramolecular hydroamination of o-alkynylanilines.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Cycloisomerization of 2‐Alkynylanilines to Indoles Catalyzed by Carbon‐Supported Gold Nanoparticles and Subsequent Homocoupling to 3,3′‐Biindoles

Cited by 103 publications

References 67 publications

On the Nature of Interactions between Ionic Liquids and Small Amino‐Acid‐Based Biomolecules

On the Nature of Interactions between Ionic Liquids and Small Amino‐Acid‐Based Biomolecules

Palladium‐Catalyzed Synthesis of Heteroarene‐Fused Cyclooctatetraenes through Dehydrogenative Cyclodimerization

A Reusable MOF‐Supported Single‐Site Zinc(II) Catalyst for Efficient Intramolecular Hydroamination of o‐Alkynylanilines

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