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Featured researches published by Nicola Della Ca.


Accounts of Chemical Research | 2008

Catalytic Sequential Reactions Involving Palladacycle-Directed Aryl Coupling Steps

Marta Catellani; Elena Motti; Nicola Della Ca

Catalytic methods are important tools for the synthesis of C-C bonds under mild and ambient conditions. Palladium chemistry predominates in this area because it offers the opportunity to form several different types of bonds in one pot. Palladium can also tolerate a variety of functional groups. Among the many investigations of catalytic aryl-aryl couplings, the most successful technique has been the Suzuki reaction, which uses an arylboronic acid to attack an aryl-Pd bond. This Account reports our methodology, based on the cooperative action of Pd and norbornene, that achieves selective aryl-aryl coupling through C-halide and C-H activation. We are primarily interested in Pd-catalyzed sequential reactions. These reactions combine palladium as an inorganic catalyst and a strained olefin such as norbornene as an organic catalyst and can lead to biphenyl derivatives. While the palladium facilitates C-C bond formation through C-halide and C-H activation, the norbornene contributes to the construction of a palladacycle, an intermediate structure that controls and directs the subsequent reaction steps selectively. To achieve regioselective arylation at the carbon ortho to the original C-halide bond, palladacycles require an additional ortho substituent (R(1)). The palladacycle opens, giving rise to a biphenylylnorbornylpalladium complex. Because of the steric hindrance exerted by the two ortho groups, norbornene deinsertion readily occurs to form a biphenylylpalladium complex. Thus, norbornene acts as a removable scaffold. We used this biphenylylpalladium species to form C-C (with olefins, alkynes, or arylboronic acids) or C-H bonds (by hydrogenolysis). Using nonidentical aryl or heteroaryl halides, we also formed a biaryl-bonded Pd species able to undergo the final termination reaction (C-C, C-N, or C-O bond formation) either inter- or intramolecularly. We used this method to synthesize a variety of aromatic and heteroaromatic compounds. We also obtained the key metallacycle able to selectively direct the reactions by replacing norbornene with an aryl-bonded aminocarbonyl group. This method provided a diverse series of condensed heterocycles.


Organic Letters | 2012

A Sequential Pd/Norbornene-Catalyzed Process Generates o-Biaryl Carbaldehydes or Ketones via a Redox Reaction or 6H-Dibenzopyrans by C–O Ring Closure

Elena Motti; Nicola Della Ca; Di Xu; Anna Piersimoni; Elena Bedogni; Zhiming Zhou; Marta Catellani

o-Biaryl carbaldeydes and ketones are obtained through the one-pot reaction of o-aryl iodides with o-bromobenzyl alcohols under the catalytic action of Pd and norbornene, in the presence of a base. The same reaction can also give dibenzopyrans by Pd and norbornene catalysis with a different termination, leading to C-O ring closure. In both cases the process first leads to a five-membered palladacycle, which controls C-C coupling, then to a seven-membered oxapalladacycle, which gives aldehydes and ketones or dibenzopyrans.


Chemical Communications | 2009

A catalytic synthesis of selectively substituted biaryls through sequential intermolecular coupling involving arene and ketone C–H bond functionalization

Giovanni Maestri; Nicola Della Ca; Marta Catellani

Selectively substituted biaryls containing a ketone unit are obtained under mild conditions in satisfactory yields by a simple reaction of ortho-substituted aryl iodides and ketones in the presence of palladium and norbornene as catalysts.


Chemsuschem | 2015

Catalytic Oxidative Carbonylation of Amino Moieties to Ureas, Oxamides, 2-Oxazolidinones, and Benzoxazolones

Raffaella Mancuso; Dnyaneshwar S. Raut; Nicola Della Ca; Francesco Fini; Carla Carfagna; Bartolo Gabriele

The direct syntheses of ureas, oxamides, 2-oxazolidinones, and benzoxazolones by the oxidative carbonylation of amines, β-amino alcohols, and 2-aminophenols allows us to obtain high value added molecules, which have a large number of important applications in several fields, from very simple building blocks. We have found that it is possible to perform these transformations using the PdI2 /KI catalytic system in an ionic liquid, such as 1-butyl-3-methylimidazolium tetrafluoroborate, as the solvent, the solvent/catalyst system can be recycled several times with only a slight loss of activity, and the product can be recovered easily by crystallization.


Journal of Organic Chemistry | 2017

Pd-Catalyzed/Iodide-Promoted α-Arylation of Ketones for the Regioselective Synthesis of Isocoumarins

Alessandra Casnati; Raimondo Maggi; Giovanni Maestri; Nicola Della Ca; Elena Motti

A variety of isocoumarins have been synthesized directly from 2-halobenzoates and ketones through a palladium-catalyzed α-arylation step followed by an intramolecular cyclization process. The addition of iodide anions to the reaction mixture increased yields and selectivities especially when 2-bromobenzoates were employed. This phosphine-free one-pot synthesis features a high functional group tolerance and gives access to richly decorated isocoumarins. This general methodology was successful in the total synthesis of Xyridin A, an important natural product with antibacterial and antifungal activity.


Chemistry: A European Journal | 2018

An Unprecedented Pd-Catalyzed Carbonylative Route to Fused Furo[3,4-b]indol-1-ones

Alessandra Acerbi; Carla Carfagna; Mirco Costa; Raffaella Mancuso; Bartolo Gabriele; Nicola Della Ca

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.


Organic Letters | 2018

Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis

Gianpiero Cera; Matteo Lanzi; Davide Balestri; Nicola Della Ca; Raimondo Maggi; Franca Bigi; Max Malacria; Giovanni Maestri

The combination of a Pd(0) complex with benzoic acid converts propargylic tryptamines to the corresponding tetrahydro-β-carbolines. The method uses unprotected indoles and affords the desired products with ample functional group tolerance. Detailed modeling studies reveal a close synergy between the organic and metal catalysts, which enables sequential alkyne isomerization, indole C-H activation, and eventual C-C reductive elimination to afford the target heterocycles.


iScience | 2018

Catalytic Double Cyclization Process for Antitumor Agents against Breast Cancer Cell Lines

Raffaella Mancuso; Ida Ziccarelli; Adele Chimento; Nadia Marino; Nicola Della Ca; Rosa Sirianni; Vincenzo Pezzi; Bartolo Gabriele

Summary The development of efficient synthetic strategies for the discovery of novel antitumor molecules is a major goal in current research. In this context, we report here a catalytic double cyclization process leading to bicyclic heterocycles with significant antitumor activity on different human breast cancer (BC) cell lines. The products, 6,6a-dihydrofuro[3,2-b]furan-2(5H)-ones, were obtained in one step, starting from simple substrates (4-yne-1,3-diols, CO, and O2), under the catalytic action of PdI2 in conjunction with KI. These compounds have significant antiproliferative activity in vitro on human BC cell lines, both hormone receptor positive (MCF-7) and triple negative (triple-negative breast cancer [TNBC]; MDA-MB-231 and MDAMB-468), while exhibiting practically no effects on normal MCF-10A (human mammary epithelial) and 3T3-L1 (murine fibroblasts) cells. Thus, these compounds have the potential to expand the therapeutic options against BC, and in particular, against its most aggressive forms (TNBCs). Moreover, the present synthetic approach may provide an economic benefit for their production.


Molbank | 2018

Cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine

Alessandra Casnati; Elena Motti; Nicola Della Ca

The title compound—cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine—was synthesized in 83% isolated yield by a palladium-catalyzed one-pot strategy from 1-iodo-2-isopropoxybenzene and ortho-bromoaniline. The azepine derivative was fully characterized (FT-IR, MS, 1H and 13C-NMR, elemental analysis) and all proton and carbon signals have been completely assigned by 2D NMR experiments.


Molbank | 2018

Dimethyl 2,2′-[Carbonylbis(azanediyl)](2S,2′S)-bis[3-(4-hydroxyphenyl)propanoate]

Raffaella Mancuso; Katia Gioia; Antonio Piccionello; Nicola Della Ca; Carla Carfagna; Bartolo Gabriele

The thus-far unknown ureic derivative dimethyl 2,2′-[carbonylbis(azanediyl)](2S,2′S)-bis[3-(4-hydroxyphenyl)propanoate] has been efficiently synthesized by enantiospecific oxidative carbonylation of readily available l-tyrosine methyl ester, using a very simple catalytic system (PdI2 in conjunction with KI) under relatively mild conditions (100 °C for 5 h in DME as the solvent and under 20 atm of a 4:1 mixture CO-air).

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