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Ruth Dorel

Ruth Dorel
Genentech · Department of Small Molecule Discovery Chemistry

PhD

About

43
Publications
8,492
Reads
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3,490
Citations
Additional affiliations
December 2020 - present
Genentech
Position
  • Senior Researcher
July 2017 - October 2020
University of Groningen
Position
  • PostDoc Position
February 2017 - June 2017
Institute of Chemical Research of Catalonia
Position
  • PostDoc Position

Publications

Publications (43)
Article
Full-text available
A unified approach to the synthesis of the series of higher acenes up to previously unreported undecacene has been developed through the on‐surface dehydrogenation of partially saturated precursors. These molecules could be converted into the parent acenes by atomic manipulation with the tip of a scanning tunneling and atomic force microscope (STM/...
Article
A novel strategy for the synthesis of partially saturated acene derivatives has been developed based on a AuI-catalyzed cyclization of 1,7-enynes. This method provides straightforward access to stable polycyclic products featuring the backbone of the acene series, up to nonacene.
Article
The total synthesis of lundurines A-C has been accomplished in racemic and enantiopure forms in 11-13 and 12-14 steps, respectively, without protection / deprotection of functional groups, by a novel tandem double condensation / Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3+2] cycloaddition / nit...
Article
Gold(I) complexes are the most effective catalysts for the electrophilic activation of alkynes under homogeneous conditions, and a broad range of versatile synthetic tools have been developed for the construction of carbon-carbon or carbon-heteroatom bonds. The properties of gold (I) complexes can be easily tuned sterically or electronically depend...
Article
Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI=NTs. Remarkably, this transformation proceeds in the presence of olefins and other functional groups without formation of the commonly observed aziridines or C-H insertion products. The methodology c...
Article
Full-text available
The phosphorus stereocentre, present in a diversity of compounds ranging from phosphonates to phosphines, plays a crucial role in various fields, in particular catalysis, materials science, agrochemistry and drug development. The unique structural and stereochemical features of intrinsically homochiral phosphorus units form the incentive for major...
Article
Full-text available
On-surface synthesis is becoming an increasingly popular approach to obtain new organic materials. In this context, metallic surfaces are the most commonly used substrates. However, their hybridization with the adsorbates often hinder a proper characterization of the molecule’s intrinsic electronic and magnetic properties. Here we report a route to...
Article
Full-text available
Unidirectional molecular rotation based on alternating photochemical and thermal isomerizations of overcrowded alkenes is well established, but rotary cycles based purely on photochemical isomerizations are rare. Herein we report three new second-generation molecular motors featuring a phosphorus center in the lower half, which engenders a unique e...
Preprint
Full-text available
We report on the effect of sp3 hybridized carbon atoms in acene derivatives adsorbed on metal surfaces, namely decoupling the molecules from the supporting substrates. In particular, we have used a Ag(100) substrate and hydrogenated heptacene molecules, in which the longest conjugated segment determining its frontier molecular orbitals amounts to f...
Article
Full-text available
A method for the nucleophilic fluorination of heptamethyl aryl trisiloxanes to form fluoroarenes is reported. The reaction proceeds in the presence of Cu(OTf)2 and KHF2 as the fluoride source under mild conditions for a broad range of heptamethyltrisiloxyarenes with high functional group tolerance. The combination of this method with the silylation...
Article
Full-text available
A photoresponsive chiral catalyst based on an oligotriazole‐functionalized unidirectional molecular motor has been developed for stereodivergent anion binding catalysis. The motor function controls the helical chirality of supramolecular assemblies with chloride anions, which by means of chirality transfer enables the enantioselective addition of a...
Article
Full-text available
Genug Hubraum für Katalyse: Ein photoresponsiver chiraler Katalysator, der auf einem Oligotriazol‐funktionalisierten unidirektionalen molekularen Motor basiert, wurde für die stereodivergente Anionenbindungskatalyse entwickelt. Die Motorfunktion kontrolliert die helikale Chiralität supramolekularer Anordnungen mit Chlorid‐Anionen. Abstract A photo...
Article
The quest for organic materials with improved optoelectronic properties has stimulated the development of new strategies for the preparation of polycyclic aromatic hydrocarbons. Within this context, transition metal catalysis offers unparalleled opportunities for the assembly of complex molecular architectures. The palladium-catalyzed direct C-H ar...
Article
The Pd‐catalyzed coupling of aryl (pseudo)halides and amines is one of the most powerful approaches for the construction of C(sp2)–N bonds. Since the pioneering reports from Migita and subsequently Buchwald and Hartwig, this methodology now known as the Buchwald–Hartwig amination has experienced a continuous development towards general and practica...
Article
Full-text available
The Pd‐catalyzed coupling of aryl (pseudo)halides and amines is one of the most powerful approaches for the formation of C(sp²)−N bonds. The pioneering reports from Migita and subsequently Buchwald and Hartwig on the coupling of aminostannanes and aryl bromides rapidly evolved into general and practical tin‐free protocols with broad substrate scope...
Article
Full-text available
Photoswitchable catalysis is a young but rapidly evolving field that offers great potential for non-invasive dynamic control of both activity and selectivity in catalysis. Within this context, the E/Z photoisomerisation of double bonds in molecular switches and motors is one of the most popular tools to control the catalytic activity essentially du...
Poster
The analysis of reactant, intermediates and end product heptacene reveals the dependence of band gap, stability and molecular charge state on the extent of the longest conjugated acene segment. For intermediate 2, featuring a pentacene segment, the appearance and behavior of charging peaks and a zero-bias anomaly are all in good agreement with a sc...
Article
Achieving the Ag(001)-supported synthesis of heptacene from two related reactants reveals the effect of the presence of Br atoms on the reaction process. The properties of reactants, intermediates and end-products are further characterized by scanning tunneling microscopy and spectroscopy.
Preprint
Full-text available
Achieving the Ag(001)-supported synthesis of heptacene from two related reactants reveals the effect of the presence of Br atoms on the reaction process. The properties of reactant, intermediates and end-product are further characterized by scanning tunneling microscopy and spectroscopy.
Article
Full-text available
The design and synthesis of an overcrowded-alkene based molecular motor featuring a crown ether integrated in its stator structure has been accomplished. The photostationary state ratios and rotational speed of this motor can be modulated by cation coordination to the crown ether moiety, which can be reversed upon the addition of a competing chelat...
Article
Full-text available
A unified approach to the synthesis of the series of higher acenes up to previously unreported undecacene has been developed through the on‐surface dehydrogenation of partially saturated precursors. These molecules could be converted into the parent acenes by atomic manipulation with the tip of a scanning tunneling and atomic force microscope (STM/...
Article
Full-text available
The alkynylation of naphthols takes place with total regiocontrol at the peri position of the hydroxyl group in the presence of [RuCl2(p-cymene)]2 as the catalyst. This reaction features high functional group tolerance. The related ortho-alkynylation of benzoic acids proceeds under similar conditions and also shows wide functional group tolerance....
Article
The on-surface synthesis of nonacene has been accomplished by dehydrogenation of an air-stable partially saturated precursor, which could be aromatized by using a combined scanning tunneling and atomic force microscope (STM/AFM) as well as by on-surface annealing. This transformation allowed the in-detail analysis of the electronic properties of no...
Article
The cover picture shows a few acene precursors in the background and several acenes projected on a nest of European paper wasps (Polistes dominula) photographed by one of the authors (A. M. E.) at the Platja Llarga (long beach) in Tarragona, Spain. Coincidentally, the wasps, like other Hymenoptera insects, are very good at synthesizing diverse hydr...
Article
Full-text available
The outstanding performance of pentacene-based molecules in molecular electronics, as well as the predicted enhanced semiconducting properties of extended acenes, have stimulated the development of new synthetic methods and functionalization strategies for the preparation of stable and soluble acenes larger than tetracene with the aim of obtaining...
Article
Full-text available
The [3,5,5,7] tetracyclic skeleton of echinopines has been stereoselectively accessed through a gold(I)-catalyzed alkoxycyclization of cyclopropyl-tethered 1,6- enynes. The key bicycle[4.2.1]nonane core of the enyne precursors was readily assembled by means of a Co-catalyzed [6+2] cycloaddition. Furthermore, the attempted alkoxycyclization of 1,5-e...
Article
Full-text available
A novel strategy for the synthesis of partially saturated acene derivatives has been developed based on a Au(I) -catalyzed cyclization of 1,7-enynes. This method provides straightforward access to stable polycyclic products featuring the backbone of the acene series, up to nonacene.
Article
Full-text available
The synthesis of a new C3v-symmetric crushed fullerene C60H24 (5) has been accomplished in three steps from truxene through sixfold palladium-catalyzed intramolecular arylation of a syn-trialkylated truxene precursor. Laser irradiation of 5 induces cyclodehydrogenation processes that result in the formation of C60, as detected by LDI-MS.
Article
Methods for the highly stereoselective and regiodivergent hydrosilylation of 1,3‐disubstituted allenes have been developed. The synthesis of E allylsilanes is accomplished with palladium NHC catalysts, and trisubstituted Z alkenylsilanes are accessed with nickel NHC catalysts. Unsymmetrically substituted allenes are well tolerated with nickel catal...
Article
Methods for the highly stereoselective and regiodivergent hydrosilylation of 1,3-disubstituted allenes have been developed. The synthesis of E allylsilanes is accomplished with palladium NHC catalysts, and trisubstituted Z alkenylsilanes are accessed with nickel NHC catalysts. Unsymmetrically substituted allenes are well tolerated with nickel catal...
Article
Cycloisomerizations of 1,n-enynes catalyzed by gold(I) proceed via electrophilic species with a highly distorted cyclopropyl gold(I) carbene-like structure, which can react with different nucleophiles to form a wide variety of products by attack at the cyclopropane of the carbene carbons. Particularly important are reactions in which the gold(I) ca...
Article
Full-text available
A new disc-shaped highly symmetric C54H20 nanographene fragment, tetrabenzocircumpyrene, has been synthesized and characterized by scanning tunnelling microscopy, demonstrating the potential of this technique for identifying highly insoluble graphenic molecules.
Article
A diastereoselective synthesis of cis-5-oxodecahydroquinolines is described in which three stereocenters are generated in a one-pot reaction. The reaction involves a lithium hydroxide-promoted Robinson annulation/intramolecular aza-Michael domino process from an achiral acyclic tosylamine-tethered β-keto ester. The development and scope of this rea...

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