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5. Palladium‐Catalyzed Carbonylation of Multifunctionalized Substituted Alkynes to Quinolinone Derivatives under Mild Conditions

Author

Voronov, Aleksandr, primary, Pancrazzi, Francesco, additional, Constantin, Ana Maria, additional, Maggi, Raimondo, additional, Mancuso, Raffaella, additional, Gabriele, Bartolo, additional, Olivieri, Diego, additional, Carfagna, Carla, additional, Casnati, Alessandro, additional, Rispoli, Francesco, additional, Baldini, Laura, additional, and Della Ca’, Nicola, additional

Published
2023
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7. Palladium‐Catalyzed Carbonylation of Multifunctionalized Substituted Alkynes to Quinolinone Derivatives under Mild Conditions†.

Author

Voronov, Aleksandr, Pancrazzi, Francesco, Constantin, Ana Maria, Maggi, Raimondo, Mancuso, Raffaella, Gabriele, Bartolo, Olivieri, Diego, Carfagna, Carla, Casnati, Alessandro, Rispoli, Francesco, Baldini, Laura, and Ca, Nicola Della

Abstract

Comprehensive Summary: A highly selective palladium‐catalyzed carbonylation of 2‐alkynylanilines bearing an amide moiety to condensed six‐membered heterocyclic structures has been developed under mild conditions (room temperature and atmospheric pressure of CO). The carbonylative protocol is also compatible with CO surrogates, such as benzene‐1,3,5‐triyl triformate (TFBen) or the newly developed calix[6]arenes functionalized with six formate groups (CLX[6]CO), which are both capable to release CO in situ. A series of tricyclic fused heterocycles containing the important oxazino‐quinolinone scaffold have been selectively obtained (only the 6‐endo‐dig cyclization mode has been observed) in good to excellent yields (up to 99%). [ABSTRACT FROM AUTHOR]

Published
2023
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13. Dibenzyl-(1 S *,2 S *)-2,3-dihydro-1 H -indene-1,2-dicarboxylate.

Author

Olivieri, Diego, Tarroni, Riccardo, and Carfagna, Carla

Subjects
BENZYL alcohol, CARBON monoxide, ALCOHOL oxidation, SUCCINIC acid, HOMOGENEOUS catalysis, SUCCINATES
Abstract

The synthesis of dibenzyl-(1S*,2S*)-2,3-dihydro-1H-indene-1,2-dicarboxylate has been realized through a diastereospecific bis-alkoxycarbonylation reaction, which starts from the cheap and easily available 1H-indene, benzyl alcohol, and carbon monoxide. The catalyst is formed in situ by mixing Pd(TFA)2, the ligand N2,N3-bis(2,6-dimethylphenyl)butane-2,3-diimine, p-benzoquinone is used as an oxidant, and benzyl alcohol acts both as a nucleophile and as the main solvent. [ABSTRACT FROM AUTHOR]

Published
2023
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15. Palladium Catalyzed Bis-Alkoxycarbonylation of Variously Substituted Alkenes

Author

Diego Olivieri, RICCARDO TARRONI, Gabriele, Manca, Carlo, Mealli, Carfagna, Carla, Diego Olivieri, Riccardo Tarroni, Gabriele Manca, Carlo Mealli, and Carla Carfagna

Subjects
nitrogen ligand, DFT studies, bis-alkoxycarbonylation, palladium catalysis, carbonylation, palladium catalysi
Published
2020

16. Bis-Alkoxycarbonylation And Difunctionalization Of Alkenes Employing Palladium(II) Or Nickel(II) Complexes As Catalysts

Author

Carfagna, Carla, Olivieri, Diego <1992>, Carfagna, Carla, and Olivieri, Diego <1992>

Abstract

Section 1 is focused on the bis-alkoxycarbonylation reaction of olefins, catalyzed by aryl α-diimine/Pd(II) complexes, for the synthesis of succinic acid ester derivatives, important compounds in many industrial fields. The opening chapter (Chapter 1) of this thesis presents an overview of the basic chemistry of organopalladium compounds and carbonylation reactions, focusing on oxidative bis-alkoxycarbonylation processes. In Chapter 2 the results obtained in the bis-alkoxycarbonylation of 1,2-disubstituted olefins are reported. The reaction proceeds under very mild reaction conditions, using an aryl α-diimine/Pd(II) catalyst and p-benzoquinone as oxidant, in the presence of a suitable alcohol. This process proved to be very efficient, selective and diastereospecific and various 2,3-disubstituted succinic esters have been obtained in high yields. In Chapter 3 the first bis-alkoxycarbonylation reaction of acrylic esters and acrylic amides, leading to the synthesis of 2-alkoxycarbonyl and 2-carbamoyl succinates respectively, is reported. Remarkably, the utilized aryl α-diimine/Pd(II) catalyst is able to promote the carbonylation of both the β- and the generally non-reactive α- positions of these alkenes. The proposed catalytic cycle is supported by DFT calculations. Section 2 is mainly focused on the Ni-catalyzed difunctionalization of unactivated alkenes tethered to unstabilized ketones. This reaction allows for a wide range of pharmaceutically useful cyclic architectures to be obtained. Chapter 4 consists of an introduction to the difunctionalization reactions of unactivated olefins. In particular, intramolecular reactions will be discussed in detail. In Chapter 5 the results obtained from the Ni-catalyzed difunctionalization of unactivated alkenes tethered to unstabilized ketones are reported. The reaction proceeds through the formation of a zinc-enolate compound, followed by a cyclization/cross-coupling reaction, which takes place in the presence of a phosphine/Ni(

Published
2020

27. Stereoselective palladium-catalyzed bis-alkoxycarbonylation of internal olefins

Author

Olivieri, Diego, Francesco, Fini, Mazzoni, Rita, Zanotti, Valerio, Carfagna, Carla, Diego, Olivieri, Francesco, Fini, Rita, Mazzoni, Valerio, Zanotti, and Carla, Carfagna

Subjects
olefins, aryl alpha-diimine ligands, bis-alkoxycarbonylation, olefins, Palladium, aryl alpha-diimine ligands, Palladium, bis-alkoxycarbonylation
Published
2017

29. Bis‐Alkoxycarbonylation of Acrylic Esters and Amides for the Synthesis of 2‐Alkoxycarbonyl or 2‐Carbamoyl Succinates.

Author

Olivieri, Diego, Tarroni, Riccardo, Della Ca', Nicola, Mancuso, Raffaella, Gabriele, Bartolo, Spadoni, Gilberto, and Carfagna, Carla

Subjects
AMIDE synthesis, SUCCINATES, ESTERS, CARBON monoxide, CARBONYLATION, ACRYLIC acid
Abstract

The first example of the bis‐alkoxycarbonylation of acrylic esters and acrylic amides, leading to differently substituted 1,1,2‐ethanetricarboxylate compounds and 2‐carbamoylsuccinates respectively, is reported. The catalyst is formed in situ by mixing Pd(TFA)2 (TFA=trifluoroacetate) and the ligand bis(2,6‐dimethylphenyl)butane‐2,3‐diimine. The reaction, that proceeds using p‐benzoquinone as oxidant and p‐toluenesulfonic acid as additive, has been applied to variously substituted electron‐poor alkenes, employing different alcohols as nucleophiles, under very mild reaction conditions (4 bar of carbon monoxide at 20 °C). Remarkably, this catalytic system is able to promote the carbonylation of both the β‐ and the generally unreactive α‐positions of acrylic esters and amides, allowing the formation of bis‐alkoxycarbonylated products in good to excellent yields (up to 98%). The trend of reactivity, observed with the different electron‐deficient olefins, has been rationalized on the basis of the proposed catalytic cycle and DFT calculations. [ABSTRACT FROM AUTHOR]

Published
2020
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31. Front Cover Picture: Diastereospecific Bis-alkoxycarbonylation of 1,2-Disubstituted Olefins Catalyzed by Aryl α-Diimine Palladium(II) Catalysts (Adv. Synth. Catal. 18/2018)

Author

Olivieri, Diego, primary, Fini, Francesco, additional, Mazzoni, Rita, additional, Zacchini, Stefano, additional, Della Ca', Nicola, additional, Spadoni, Gilberto, additional, Gabriele, Bartolo, additional, Mancuso, Raffaella, additional, Zanotti, Valerio, additional, and Carfagna, Carla, additional

Published
2018
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36. A novel Catalytic System for the Divergent Oxidative Carbonylation of Alkynes into Propiolic or Maleic Esters. (Inside Back Cover)

Author

Beltrani, M., Milani, B., Mancuso, R., Gabriele, B., Fini, F., CARFAGNA, CARLA, Beltrani, M., Carfagna, C., Milani, B., Mancuso, R., Gabriele, B., and Fini, F.

Subjects
Palladium catalysts, carbonylation of alkynes, Propiolic and maleic esters
Abstract

The inside cover picture shows a catalytic cycle, in which an in situ generated bis(2,6-diisopropyl)acenaphthenequinonediimine palladium catalyst is able to divergently convert terminal and internal alkynes into propiolic esters or maleic esters and their derivatives, respectively, with a wide range of alcohols, under oxidative alkoxycarbonylation conditions (4 bar of carbon monoxide, in the presence of benzoquinone as oxidant at 20 °C).

Published
2016

37. A Regio‐ and Stereoselective Carbonylative Approach to Alkyl (Z)‐2‐[3‐Oxoisobenzofuran‐1‐(3H)‐ylidene]acetates.

Author

Mancuso, Raffaella, Ziccarelli, Ida, Fini, Francesco, Della Ca', Nicola, Marino, Nadia, Carfagna, Carla, and Gabriele, Bartolo

Subjects
ACETATES, BENZOFURANS, STEREOSELECTIVE reactions, RING formation (Chemistry), CATALYTIC activity, CHEMICAL yield, BENZOIC acid
Abstract

The first example of the oxidative carbonylation of 2‐ethynylbenzoic acid derivatives, leading to alkyl (Z)‐2‐[3‐oxoisobenzofuran‐1‐(3H)‐ylidene]acetates in a regio‐ and stereoselective manner, is reported. Under the catalytic action of PdI2 (2 mol%) in conjuction with KI (20 mol%), different 2‐[(trimethylsilyl)ethynyl]benzoic acids were converted into the corresponding isobenzofuranones in high to excellent yields (70–98%). The proposed reaction mechanism involves syn 5‐exo‐dig cyclization, carbon monoxide insertion, and nucleophilic displacement by an alcohol. Desilylation occurred under the reaction conditions. The structure of a representative product, that is, methyl (Z)‐2‐[3‐oxoisobenzofuran‐1(3H)‐ylidene]acetate, was confirmed by XRD analysis. [ABSTRACT FROM AUTHOR]

Published
2019
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42. An Unprecedented Pd‐Catalyzed Carbonylative Route to Fused Furo[3,4‐<italic>b</italic>]indol‐1‐ones.

Author

Acerbi, Alessandra, Carfagna, Carla, Costa, Mirco, Mancuso, Raffaella, Gabriele, Bartolo, and Della Ca', Nicola

Subjects
*PALLADIUM, *CARBON monoxide, *RING formation (Chemistry), *HETEROCYCLIC compounds, *MOLECULES
Abstract

Abstract: A novel and efficient catalytic approach to functionalized furo[3,4‐b]indol‐1‐ones is reported. It is based on a palladium‐catalyzed sequential process involving an initial cyclization of 2‐(hydroxypropyn‐1‐yl)anilines to form the indole moiety, followed by insertion of carbon monoxide and a second annulation step to build a lactone ring. In a single transformation, two fused heterocycles and three new bonds (C−N, C−C and C−O) are generated. The present methodology gives direct access to structurally complex molecules starting from readily available reagents. [ABSTRACT FROM AUTHOR]

Published
2018
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