Eduardo Carmelo Escudero-Adán

Eduardo Carmelo Escudero-Adán
ICIQ Institute of Chemical Research of Catalonia | ICIQ · Characterization Technologies Department - CTD

PhD

About

193
Publications
12,346
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7,124
Citations
Citations since 2016
71 Research Items
4706 Citations
20162017201820192020202120220200400600800
20162017201820192020202120220200400600800
20162017201820192020202120220200400600800
20162017201820192020202120220200400600800
Introduction
Dr. Eduardo C. Escudero-Adán currently works as laboratory manager at the X-ray Diffraction Unit, ICIQ Institute of Chemical Research of Catalonia. Eduardo does research in Solid-state Chemistry, Supramolecular Chemistry and Surface Chemistry.
Additional affiliations
November 2004 - December 2012

Publications

Publications (193)
Article
A new catalytic route has been developed for the coupling of epoxides and CO2 affording polymerizable six‐membered bicyclic carbonates. Cyclic epoxides equipped with a b‐positioned OH group can be transformed into structurally diverse bicyclic cyclic carbonates in good yields and with high selectivity. Key to the chemo‐selectivity is the difference...
Article
Full-text available
A new catalytic route has been developed for the coupling of epoxides and CO2 affording polymerizable six‐membered bicyclic carbonates. Cyclic epoxides equipped with a b‐positioned OH group can be transformed into structurally diverse bicyclic cyclic carbonates in good yields and with high selectivity. Key to the chemo‐selectivity is the difference...
Article
The Cover Feature shows a photocatalytic reductive dimerization reaction promoted by a post‐functionalized MOF with a perylene photosensitizer. Blue light irradiation selectively excites the perylene units that behave as isolated catalysts, anchored in well‐defined positions inside the MOF pores. More information can be found in the Full Paper by L...
Article
A novel approach to modify the SBU of the well-known bio-MOF-1 by reducing the nuclearity of the metal cluster while retaining the topology of the anionic 3D framework is reported....
Article
Post‐modification of reticular materials with well‐defined catalysts is an appealing approach to produce new catalytic functional materials with improved stability and recyclability, but also to study the catalysis phenomena in confined spaces. A promising strategy to this end is the post‐functionalization of crystalline and robust metal‐organic fr...
Preprint
Valorization of carbon dioxide into organic molecules using catalytic approaches has witnessed an upsurge in recent years. Here, the influence of an Al(III) aminotriphenolate complex on the regio- and stereo-chemical features of the coupling between carbon dioxide and a cyclic epoxy alcohol has been studied. Three distinct bicyclic carbonate produc...
Article
Full-text available
This manuscript reports the improved synthesis of the α,α,α,α isomer of tetra-p-iodophenyl tetra-methyl calix[4]pyrrole and the X-ray characterization of two solvate polymorphs. In the solid state, the calix[4]pyrrole receptor adopts the cone conformation, including one acetonitrile molecule in its aromatic cavity by establishing four convergent hy...
Article
Planar pyridyl N‐oxides are encapsulated in mono‐metallic Pd(II)/Pt(II)‐cages based on a tetra‐pyridyl calix[4]pyrrole ligand. The exchange dynamics of the cage complexes are slow on both the NMR chemical shift and EXSY timescales, but encapsulation of the guests by the cages is fast on the human timescale. A “french doors” mechanism, involving the...
Article
Planare N-Oxide sind in monometallische PdII/PtII-Käfige eingekapselt. Die Ein-/Umlagerung der planaren Gäste erfolgt über einen „Fenstertür”-Mechanismus. Der PdII-Käfig kann von diesem Mechanismus zu einem Mechanismus der teilweisen Ligand-Metall-Dissoziation wechseln, um ein sterisch anspruchsvolles N-Oxid einzulagern. Dennoch wird der sterisch a...
Article
Selective separation of enantiomers is a substantial challenge for the pharmaceutical industry. Chromatography on chiral stationary phases is the standard method, but at a very high cost for industrial-scale purification owing to the high cost of the chiral stationary phases. Typically, these materials are poorly robust, expensive to manufacture an...
Article
Tertiary allylic alcohols are conveniently converted into either (Z)‐ or (E)‐configured alfa,beta‐unsaturated gamma‐amino acids by treatment with secondary amines under Pd catalysis at ambient conditions. Key to control the stereoselective course of these formal allylic aminations is the presence of a suitable diphosphine ligand, with dppp [1,3‐dip...
Article
Full-text available
The identification of catalytic intermediates in the conversion of carbon dioxide is vital for improved catalyst design and optimization of structure–reactivity relationships, but remains elusive. Here, we report that intermolecular hydrogen bonding interactions between an epoxy alcohol, water and the catalyst structure are crucial towards the form...
Article
The tetra-α isomer of a super aryl-extended tetra-pyridyl calix[4]pyrrole self-assembles into a mono-metallic Pd(II)-cage featuring two different and converging polar binding sites. Mono- and di-topic polar guests are bound reversibly...
Article
X-ray charge density was determined and analysed for two polymorphs of the N-methylpyridinium salt of the tetrachlorosemiquinone radical anion and its analogous closed-shell relatives, tetrachloroquinone (chloranil) and tetrachlorohydroquinone. The study, which was combined with calculations of electron delocalization, electrostatic potentials, and...
Article
Tertiary allylic alcohols equipped with a carboxyl group can be smoothly aminated under ambient conditions via a conceptually new and stereoselective protocol under Pd catalysis. The in situ formed (Z)‐configured alfa‐amino acid cyclizes to afford an alfa,beta‐unsaturated gamma‐lactam releasing water as the only by‐product. This practical catalytic...
Article
Tertiary allylic alcohols equipped with a carboxyl group can be smoothly aminated under ambient conditions via a conceptually new and stereoselective protocol under Pd catalysis. The in situ formed (Z)‐configured alfa‐amino acid cyclizes to afford an alfa,beta‐unsaturated gamma‐lactam releasing water as the only by‐product. This practical catalytic...
Article
We report the synthesis of a macrocyclic receptor containing two di-meso-phenyl calix[4]pyrrole units linked by two triazole spacers. The 1,4-substitution of the 1,2,3-triazole spacers conveys different binding affinities to the two hetero-ditopic bind-ing sites. These features make the receptor an ideal candidate to investigate allosteric cooperat...
Article
Full-text available
An innovative approach to position‐selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeds within the Hofmann‐Löffler manifold with amidyl radicals as the sole mediators to induce selective 1,5‐ and 1,6‐hydrogen atom transfer followed by halogenation. Multiple halogenation events of up to four innate C‐H bond f...
Article
Small peptides and peptomimetic compounds are valuable tools to probe and study biological systems. Small synthetic peptide analogs adopt a given secondary structure driven by structural modules that organize the compound architecture. Among them, β‐and α‐turn mimetics are widely used. We have developed SQ4 and SQ5 squaramido‐based turn modules tha...
Article
In an effort to describe π-hole interactions, we undertook accurate high-resolution X-ray diffraction analyses of single crystals of 1,4-dinitrobenzene, a co-crystal of cis-tartaric acid and bis-pyridine N-oxide and the hydrochloride of B-4-pyridinylboronic acid. We selected these three compounds owing to the π-hole accessibility features that the...
Article
Nitroalkanes undergo decarboxylative allylation in the presence of vinyl-substituted cyclic carbonates providing a wide variety of functionalized homoallylated compounds with exquisite stereocontrol. This Pd-mediated procedure features operational simplicity, versatile substrate combinations and also allows for the sequential introduction of differ...
Article
The charge density analysis of meloxicam sodium monohydrate [sodium 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide monohydrate] was performed with high-resolution X-ray diffraction data measured at low temperature (90 K). The experimental results were compared with those derived from the correspondi...
Article
Eine organokatalytische Dominosequenz für den Aufbau von Heterocyclen basiert auf der Verwendung von Kohlendioxid und Epoxyalkoholen als Reagentien. In ihrer Zuschrift (DOI: 10.1002/ange.201803967) beschreiben A. W. Kleij et al. eine Reaktion, die an die Payne‐Umlagerung von Epoxiden erinnert. Aus hoch substituierten Epoxyalkoholen werden durch sub...
Article
The Front Cover shows the ultrahigh‐resolution X‐ray diffraction of a new CuI complex with the tripodal triphosphine ligand HTIM(PPh2)3, which has the shortest well‐described Cu···H–C bond so far [d(Cu–H) = 1.9 Å]. Both theoretical and experimental studies indicate a 3c–4e– anagostic interaction. The four hands under the X‐ray radiation symbolize t...
Article
Invited for the cover of this issue is the group of Julio Lloret‐Fillol from ICIQ, Tarragona, Spain. The cover image shows the X‐ray crystallographic structure of a copper complex held by four hands. The four hands under the X‐ray radiation symbolize the team effort behind this work… Read more about the story behind the cover in the Cover Profile a...
Article
An organocatalytic domino process was developed towards elusive heterocyclic compounds that is based on the use of carbon dioxide and epoxy alcohols as reagents. In their Communication (DOI: 10.1002/anie.201803967), A. W. Kleij and co‐workers report a process reminiscent of the well‐known Payne rearrangement of epoxides. Highly substituted epoxy al...
Article
Full-text available
Estimating uncertainties of property values derived from a charge-density model is not straightforward. A methodology, based on calculation of sample standard deviations (SSD) of properties using randomly deviating charge-density models, is proposed with the MoPro software. The parameter shifts applied in the deviating models are generated in order...
Article
An unprecedented organocatalytic approach towards highly substituted cyclic carbonates from tri‐ and tetra‐substituted oxiranes and carbon dioxide has been developed. The protocol involves the use of a simple and cheap superbase under mild, additive‐ and metal‐free conditions towards the initial formation of a less substituted carbonate product tha...
Article
An unprecedented organocatalytic approach towards highly substituted cyclic carbonates from tri‐ and tetra‐substituted oxiranes and carbon dioxide has been developed. The protocol involves the use of a simple and cheap superbase under mild, additive‐ and metal‐free conditions towards the initial formation of a less substituted carbonate product tha...
Article
We present the first example of a non‐classical hydrogen bonding study for CuI complexes. To this end, we have studied the coordination capacity of the tripod phosphine ligands HTIM(PR2)3 (tris[1‐(di‐R‐phosphino)‐3‐methyl‐1H‐indol‐2‐yl]methane, R = Ph, iPr) leading to a series of eight CuI complexes [HTIM(PR2)3CuX] (R = Ph (1‐4), iPr (5‐8); X = Cl¯...
Article
Both enantiomers of the optically pure Secondary Phosphine Oxide (SPO) t-BuMeP(O)H (1) have been obtained by deboronation of phosphinous acid-borane t-BuMeP(O)H·BH3 (3) with HBF4 followed by hydrolysis of the intermediate adduct t-BuMeP(O)H·BF3 (1·BF3), which has been isolated and crystallographically characterised. Complexes [MCl(COD)(κP-(R)-1)] (...
Article
Bifunctional aminotriphenolate complexes derived from trivalent metals (M = Co, Mn, Cr) have been prepared and structurally characterized. These complexes are octahedral in the solid state but infer dynamic behavior of the ligated dimethylaminopyridine (DMAP) ligands that can function as initiators in the ring-opening copolymerization of cyclic anh...
Article
A general methodology for the synthesis of enantioenriched tertiary allylic aryl ethers through Pd-catalyzed decarboxylative reactions of vinyl cyclic carbonates and phenols is presented. Switching of the regioselectivity toward the formation of linear products by a judicious choice of the ligand is also reported.
Article
The present study investigates a synthetically simple ferrocene derivatization of natural products and active pharmaceutical ingredients. Seven new crystal structures are analyzed together with 16 structures of ferrocene derivatives reported previously. In all cases, the unambiguous determination of the absolute structure was established from anoma...
Article
The design and development of 5,5’-bistriazoles featuring aminomethyl substituents is discussed. An efficient synthetic procedure for the selective preparation of 4,4’-bis(aminomethyl)-5,5’-bistriazoles from commercially available propargylamine derivatives and benzyl azide has been optimized. The axial chirality of these atropisomeric heterobiaryl...
Article
Full-text available
Chiral polyimine molecular capsules with polar interiors have been prepared through template covalent dynamic self-assembly. An aryl-extended tetraaldehyde calix[4]pyrrole scaffold was condensed with suitable diamines as linkers using templates for...
Article
Trisubstituted cyclic organic carbonates with multiple though well-defined stereochemical configurations are difficult to prepare. Here we present a conceptual design towards these CO2 based synthons using hydroxyl-substituted cyclic epoxide precursors and their catalytic conversion, to afford these challenging target compounds with fused ring size...
Article
Herein we report the X-ray characterization of a pair of CCl3F (CFC-11) molecules trapped in a molecular sponge. The encapsulated molecules are arranged in two crystallographically independent relative orientations inside the channels. In one of them, uncommon C(sp3)–F···F–C(sp3) interactions between the CCl3F molecules are observed along with halo...
Article
A detailed account on the limiting factors of solvent annealed bulk-heterojunction small molecule organic solars cell is given. This account is based on the extensive characterization of solar cell devices made from a library of five diketopyrolopyrole (DPP) donor dyes. Their chemical structure is designed in such a way as to provide insights on th...
Article
Squaramides are presented as highly modular, easy to optimize and highly efficient catalysts for the conversion of epoxides and carbon dioxide into cyclic organic carbonates (COCs). The catalytic potential of these squaramides, in combination with a suitable halide nucleophile, is particularly noted when internal epoxides are examined as substrates...
Article
Vanadium(V) complexes derived from aminotriphenolate ligands are demonstrated to be highly active catalysts for the coupling of various terminal and internal epoxides with carbon dioxide to afford a series of substituted organic carbonates in good yields. Intriguingly, a V(V) complex bearing peripheral chloride groups on the ligand framework allowe...
Article
The preparation of isomeric metal-organic frameworks in which the network topology is controlled by the different covalent connectivity of the organic ligand is an important step forward in the design of new functional materials. In this context, macrocyclic organic ligands able to accommodate suitable guests in their own polar internal cavities ar...
Article
The trifluoromethyl anion CF3- has long been proposed as an intermediate in a broad variety of transformations, including nucleophilic trifluoromethylation of carbonyl compounds with Ruppert's reagent, Me3SiCF3. Until recently, however, the question remained whether CF3- can exist in a condensed phase. Although “the trifluoromethanide anion with a...
Article
We describe three unprecedented solid-state crystal structures (1–3) involving two (1) or three (2 & 3) different components: a suitable bis-porphyrin cage, a bis-pyridyl perylene derivative that is too large to bind the cage in a ditopic manner and, for 2 and 3, a fullerene (C60 and C70, respectively). Single co-crystals of the two/three component...
Article
A highly stereoselective ring opening of vinyl-substituted cyclic carbonates using water as a nucleophilic reagent gives (Z)-but-2-ene-1,4-diols.
Article
A broad spectrum of substituted carbonate substrates is subjected to aminolysis in the presence of TBD.
Article
Aluminum(III) complexes derived from aminotriphenolate ligands are shown to be excellent catalysts for the formation of cyclic sulfites from a range of (functionalized) terminal and internal epoxides, and ex situ generated sulfur dioxide. The developed catalytic protocol is characterized by its operational simplicity, wide scope in epoxide reaction...
Article
Newly synthesized bissaccharido palladium complexes are investigated as catalysts in the vicinal difunctionalization of terminal alkenes.
Article
Significant progress has been observed in recent years in the synthesis of allylic amines which are important building blocks in synthetic chemistry. Most of these processes are effective towards the preparation of allylic amines with limited potential to introduce three or four different substituents on the olefinic unit in a stereocontrolled fash...
Article
The first general catalytic and highly stereoselective formation of (Z)-1,4-but-2-ene diols is described from readily available and modular vinyl-substituted cyclic carbonate precursors using water as a nucleophilic reagent. These 1,4-diol scaffolds can be generally prepared in high yields and with ample scope in reaction partners using a simple sy...
Article
The synthesis of zirconium metal-organic frameworks (Zr MOFs) modulated by various amino acids, including l-proline, glycine, and l-phenylalanine, is shown to be a straightforward approach toward functional-group incorporation and particle-size control. High yields in Zr-MOF synthesis are achieved by employing 5 equivalents of the modulator at 120...
Article
The first general catalytic and highly stereoselective formation of (Z)-1,4-but-2-ene diols is described from readily available and modular vinyl-substituted cyclic carbonate precursors using water as a nucleophilic reagent. These 1,4-diol scaffolds can be generally prepared in high yields and with ample scope in reaction partners using a simple sy...
Article
Optimal reaction conditions are established for the selective conversion of epoxy amines (I) and CO2 into carbamates (III) or carbonates (IV).
Article
The inside cover picture, provided by Arjan W. Kleij and co-workers, illustrates an example of regio-directing: a general route towards the regio-selective formation of carbamates derived from substituted cyclic organic carbonates and amines is reported using a readily available organocatalyst (TBD; 1,5,7-triazabicyclo[4.4.0]dec-5-ene) under attrac...
Article
Palladium catalysis enables the regioselective difunctionalization of alkenes using saccharin as the nitrogen source in the initial step of aminopalladation. Depending on the reaction conditions, diamination or aminooxygenation pathways can be accessed using hypervalent iodine reagents as the terminal oxidants. The aminooxygenation of allylic ether...
Article
The imine bond has attracted much attention for the synthesis of macrocycles used to construct porous materials. In the present article, we report on the synthesis of two series of isomeric macrocyclic tetraimines based on bis-alkynylbenzene diamines. Under heterogeneous solid-liquid conditions the condensation of the diamines with isophthalaldehyd...
Article
The challenging coupling of highly substituted terpene oxides and carbon dioxide into bio-based cyclic organic carbonates catalyzed by Al(aminotriphenolate) complexes is reported. Both acyclic as well as cyclic terpene oxides were used as coupling partners, showing distinct reactivity/selectivity behavior. Whereas cyclic terpene oxides showed excel...
Article
Trans carbamates are prepared in a diastereoselective approach by a judicious one-pot combination of organic carbonates, prepared in situ, and suitable amine reagents under appropriate reaction conditions.
Article
Full-text available
Correction for ‘A crystalline sponge based on dispersive forces suitable for X-ray structure determination of included molecular guests’ by Elena Sanna et al., Chem. Sci., 2015, 6, 5466–5472.
Article
Substituted epoxy alcohols and amines allow substrate-controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2 -derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramo...
Article
Trans carbamates have been prepared in a diastereoselective approach by a judicious one-pot combination of organic carbonates, prepared in situ, and suitable amine reagents under appropriate reaction conditions. This unprecedented approach allows for stereodivergence from a single oxirane substrate with easy access to both cis and trans carbamate i...
Article
First evidence for the existence of free trifluoromethyl anion CF3 (-) has been obtained. The 3D-caged potassium cation in [K(crypt-222)](+) is inaccessible to CF3 (-) , thus rendering it uncoordinated ("naked"). Ionic [K(crypt-222)](+) CF3 (-) has been characterized by single-crystal X-ray diffraction, solution NMR spectroscopy, DFT calculations,...