Author
Fabio Marinelli
Other affiliations: University of Milan, Sapienza University of Rome
Bio: Fabio Marinelli is an academic researcher from University of L'Aquila. The author has contributed to research in topics: Palladium & Aryl. The author has an hindex of 39, co-authored 217 publications receiving 4570 citations. Previous affiliations of Fabio Marinelli include University of Milan & Sapienza University of Rome.
Topics: Palladium, Aryl, Annulation, Catalysis, Regioselectivity
Papers published on a yearly basis
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TL;DR: In this article, the reaction of o-ethynylphenols with a wide variety of unsaturated halides or triflates was studied in the presence of Pd(OAc)2(PPh3)2, CuI, and Et3N (procedure A) gave 2-vinyl and 2-arylbenzo[b]furans 7, in good to high yield, through a palladium-catalyzed coupling followed by an in situ cyclization step.
Abstract: The reaction of o-ethynylphenols 3 with a wide variety of unsaturated halides or triflates 6 in the presence of Pd(OAc)2(PPh3)2, CuI, and Et3N (procedure A) gives 2-vinyl- and 2-arylbenzo[b]furans 7, in good to high yield, through a palladium-catalyzed coupling followed by an in situ cyclization step. Small amounts of 2,3-disubstituted-benzo[b]furans 8 are usually isolated as side products. In some cases, however, compounds 8 are generated in significant yield or even as the main products. The formation of 8 can be prevented by employing alternative procedures (B and C) that use o-((trimethylsilyl)ethynyl)phenyl acetates 5 as starting building blocks. Procedure B is based on the palladium-catalyzed reaction of 5 with 6 in the presence of Pd(PPh3)4, Et3N, and n-Bu4NF, followed by the hydrolysis of the resultant coupling derivative 12 under basic conditions. Procedure C affords 7 through an in situ coupling/cyclization of 5 with 6 in the presence of Pd(PPh3)4 and KOBut. The utilization of o-alkynylphenols 9...
223 citations
TL;DR: Palladium(0)-catalysed coupling of aryl and vinyl triflates or halides with the easily available 2-ethynylaniline, followed by a palladium(II)catalysed cyclization step, provides an efficient and very versatile procedure for the synthesis of functionalyzed 2-substituted indoles.
179 citations
TL;DR: The gold-catalyzed reaction of 2-alkynyl-phenylamines with α,β-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions as discussed by the authors.
Abstract: The gold-catalyzed reaction of 2-alkynyl-phenylamines with α,β-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to different indoles can be directed by changing the 2-alkynyl-phenylamine 1/α,β-enone 3 ratio and the reaction temperature. Unusual gold-catalyzed rearrangement reaction of indoles are observed at 140 °C. New gold-catalyzed formation of propargyl-alkyl ether under mild conditions and the hydration reaction of N-acetyl-2-ethynyl-phenylamine are reported.
154 citations
TL;DR: A new efficient gold(III) catalysed synthesis of β-enaminones from 1,3-dicarbonyl compounds and ammonia/amines providing an attractive and environmental friendly alternative to the more vigorous reagents and drastic conditions of the existing methodologies is described.
149 citations
TL;DR: In this article, a new approach to the Friedlander synthesis of quinolines is described, which is readily prepared under milder conditions than in other existing methods through a gold(III)-catalysed sequential condensation/annulation reaction of o-amino aromatic carbonyls and ketones containing active methylene groups.
Abstract: A new approach to the Friedlander synthesis of quinolines is described. Polysubstituted quinolines are readily prepared under milder conditions than in other existing methods through a gold(III)-catalysed sequential condensation/annulation reaction of o-amino aromatic carbonyls and ketones containing active methylene groups.
148 citations
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3,281 citations
TL;DR: Important vinylgold intermediates, the transmetalation from gold to other transition metals, the development of new ligands for gold catalysis, and significant contributions from computational chemistry are other crucial points for the field highlighted here.
Abstract: Although homogeneous gold catalysis was known previously, an exponential growth was only induced 12 years ago. The key findings which induce that rise of the field are discussed. This includes early reactions of allenes and furanynes and intermediates of these conversions as well as hydroarylation reactions. Other substrate types addressed are alkynyl epoxides and N-propargyl carboxamides. Important vinylgold intermediates, the transmetalation from gold to other transition metals, the development of new ligands for gold catalysis, and significant contributions from computational chemistry are other crucial points for the field highlighted here.
2,792 citations
TL;DR: The ability of platinum and gold catalysts to effect powerful atom-economic transformations has led to a marked increase in their utilization and the application of platinum- and gold-catalyzed transformations in natural product synthesis is discussed.
Abstract: The ability of platinum and gold catalysts to effect powerful atom-economic transformations has led to a marked increase in their utilization. The quite remarkable correlation of their catalytic behavior with the available structural data, coordination chemistry, and organometallic reactivity patterns, including relativistic effects, allows the underlying principles of catalytic carbophilic activation by π acids to be formulated. The spectrum of reactivity extends beyond their utility as catalytic and benign alternatives to conventional stoichiometric π acids. The resulting reactivity profile allows this entire field of catalysis to be rationalized, and brings together the apparently disparate electrophilic metal carbene and nonclassical carbocation explanations. The advances in coupling, cycloisomerization, and structural reorganization—from the design of new transformations to the improvement to known reactions—are highlighted in this Review. The application of platinum- and gold-catalyzed transformations in natural product synthesis is also discussed.
1,938 citations
TL;DR: Pd on Modified Silica 159 4.5.1.
Abstract: 4.4. Pd on Modified Silica 159 4.5. Pd on Clay and Other Inorganic Materials 159 5. Stille, Fukuyama, and Negishi Reactions 159 5.1. Stille Reactions 159 5.1.1. Pd on Carbon (Pd/C) 159 5.1.2. Palladium on KF/Al2O3 159 5.1.3. Pd on Modified Silica (SiO2/TEG/Pd) 159 5.2. Fukuyama Reactions 159 5.2.1. Pd on Carbon (Pd/C) 159 5.2.2. Pd(OH)2 on Carbon (Perlman’s Catalyst) 160 5.3. Pd/C-Catalyzed Negishi Reactions 160 6. Ullmann-Type Coupling Reactions 161 6.1. Pd/C-Catalyzed Aryl−Aryl Coupling 161 6.2. Pd/C-Catalyzed Homocoupling of Vinyl Halides 162
1,900 citations
1,777 citations