Samuel Suarez-Pantiga

Samuel Suarez-Pantiga
Georg-August-Universität Göttingen | GAUG · Institute of Organic and Biomolecular Chemistry

PhD

About

50
Publications
2,305
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880
Citations
Citations since 2017
34 Research Items
580 Citations
2017201820192020202120222023020406080100
2017201820192020202120222023020406080100
2017201820192020202120222023020406080100
2017201820192020202120222023020406080100

Publications

Publications (50)
Article
Full-text available
A gold(I)-catalyzed cascade reaction for the stereoselective synthesis of sulfur- or selenium-containing indeno[1,2-b]chromene derivatives from o-(alkynyl)styrenes substituted at the triple bond with a thio- or seleno-aryl group is described. The reaction involves a double cyclization process through a proposed key gold-cyclopropyl carbene intermed...
Article
The combination of organolithium chemistry with gold catalysis has enabled the development of a synthetic strategy for accessing polysubstituted indoles and carbazoles from readily available starting materials. This method is based on a “back‐to‐front” approach from ketopyrroles, generated by intramolecular carbolithiation of N,N‐bis‐(2‐lithioallyl...
Article
Full-text available
The asymmetric synthesis of cyclopentachromenones from gold‐catalyzed reaction of readily available skipped alkenynones is described. This cascade reaction involves an initial anti‐Michael hydroarylation of the ynone moiety to form a gold‐functionalized dialkenylketone intermediate, followed by a Nazarov cyclization that proceeds in an unprecedente...
Article
The asymmetric synthesis of cyclopentachromenones from gold‐catalyzed reaction of readily available skipped alkenynones is described. This cascade reaction involves an initial anti‐Michael hydroarylation of the ynone moiety to form a gold‐functionalized dialkenylketone intermediate, followed by a Nazarov cyclization that proceeds in an unprecedente...
Article
A tandem 1,3‐sulfur migration followed by iodocyclization reaction of propargylic sulfides in the presence of NIS in HFIP has been developed to synthesize indene‐based β‐iodoalkenyl sulfides. The choice of the reaction media is crucial to promote the reaction. The proposed mechanism involving the initial NIS activation by HFIP and favoring the sulf...
Article
Full-text available
A straightforward and transition metal-free one-pot protocol to synthesize halobenzo[b]furans has been developed employing simple and easily available starting materials such as O-aryl carbamates and alkynylsulfones. The fine-tuning of the different steps involved was key to achieving a successful one-pot procedure. Initially, a directed ortho-lith...
Article
Dioxomolybdenum(VI) complexes have been applied as efficient, inexpensive and benign catalysts to deoxygenation reactions of a diverse number of compounds in the last two decades. Dioxomolybdenum complexes have demonstrated wide applicability to the deoxygenation of sulfoxides into sulfides and reduction of N-O bonds. Even the challenging nitro fun...
Article
Propargylic alcohols, functionalized with a 1‐(indol‐3‐yl)‐1‐(thioorganolyl)methyl substituent at the α‐position, undergo a complex but selective gold‐catalyzed transformation that gives rise to α‐indol‐3‐yl α‐((Z)‐2‐thioalkenyl) ketones. The sequence is triggered by the regioselective thiolation of indolyl diols followed by an attack of the sulfur...
Article
Like the arms of a dancer, which are waved following the rhythm of the music but avoid colliding with her head or her body; the flexible arms of expanded helicenes find different pathways to reverse their position depending on the size and nature of the insert placed in the innermost zone of their fjord. This work presents the synthesis of a series...
Article
Full-text available
A catalytic domino reduction−imine formation−intramolecular cyclization−oxidation for the general synthesis of a wide variety of biologically relevant N‐polyheterocycles, such as quinoxaline‐ and quinoline‐fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has pr...
Article
Full-text available
A series of expanded helicenes of different sizes and shapes incorporating phenyl‐ and biphenyl‐substituents at the inner part of their fjord have been synthesized via sequential Au‐catalyzed hydroarylation of appropriately designed diynes, and their racemization barriers have been calculated employing electronic structure methods. These show that...
Article
α-Oxyketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol-Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excellent stereocontrol in the generation of a quaternary...
Article
Full-text available
This work describes the 6-endo-dig cyclization of S-aryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing intramolecular silver-catalyzed alkyne hydroarylation and N-iodosuccinimide-promoted iodoarylation. Additionally, a PTSA-catalyzed thiolation reaction of propargylic al...
Article
α-Lithiobenzyl ethers, generated by selective α-lithiation, undergo an aldol-Tishchenko reaction upon treatment with carboxylic esters and paraformaldehyde. The reaction of the organolithium with the carboxylate generates an intermediate enolate that, after formaldehyde addition, affords 1,2,3-triol derivatives in a straightforward and one-pot mann...
Article
Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration-oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology...
Article
The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O→N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as dire...
Article
The α-lithiobenzyloxy group, easily generated from aryl benzyl ethers by selective α-lithiation with t-BuLi at low temperature, behaves as a directed metalation group (DMG) providing a direct access to o-lithiophenyl α-lithiobenzyl ethers. This ortho-directing effect is reinforced in substrates bearing an additional methoxy group at the meta positi...
Article
A straightforward and efficient synthesis of the two less explored types of indolocarbazoles has been developed. Two different processes for the carbazole nucleus preparation, a gold-catalysed regioselective cyclization followed by the dioxomolybdenum-catalysed version of Cadogan reductive cyclization, enables the sequential construction of two car...
Article
The first general regio‐ and stereoselective 5‐exo gold(I)‐catalyzed alkoxycyclization of a specific class of 1,5‐enynes such as 1,3‐dien‐5‐ynes has been described, despite 1,5‐enynes being known to almost invariably proceed via endo cyclizations under gold‐catalysis. The configuration of the terminal alkene in the starting 1,3‐dien‐5‐yne plays a c...
Article
Full-text available
Rhodium(II) carboxylates are privileged catalysts for the most challenging carbene-, nitrene-, and oxo-transfer reactions. In this work, we address the strategic challenges of current organic and inorganic synthesis methods to access these rhodium(II) complexes through an oxidative rearrangement strategy and a reductive ligation reaction. These stu...
Article
The stereospecific gold(I)-catalyzed nucleophilic cyclization of β-monosubsituted o-(alkynyl)styrenes to produce C-1 functionalized 1H-indenes including challenging substrates and nucleophiles, such as β-(cyclo)alkyl-subsituted o-(alkynyl)styrenes and a variety of alcohols as well as selected electron-rich aromatics, is reported. DFT calculations s...
Article
Full-text available
The oxidative rearrangment of 1,3-diketones is an underexplored alternative to enolate chemistry in the synthesis of all-carbon quaternary carboxylates. The mechanistic investigation of this reaction has resulted in a mild...
Article
The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C‐N co...
Article
The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C‐N co...
Article
Ethyl lactate, a sustainable feedstock, serves as a highly attractive building block for the synthesis of value-added chemicals such as skipped diynones and, after gold-catalyzed transposition, conjugated diynones. Green solvents...
Article
The cross-coupling reaction of alkenyl bromides with thiols catalyzed by palladium complexes derived from inexpensive dppf ligand is reported. These reactions occur under low catalyst loading and in high yields and display wide scope, including the coupling of bulky thiols and trisubstituted bromoolefins, and functional group tolerance. In addition...
Article
The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus-Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitr...
Article
Polysubstituted quinolines have been efficiently synthesized from nitroarenes and glycols, as reducing agents, under dioxomolybdenum(VI)‐catalysis. Interestingly, the waste reduction byproduct is incorporated into the final heterocycle. This method represents an efficient and sustainable variant of the Friedländer synthesis of quinolines.
Article
The gold(I)-catalyzed oxycyclization of β-aryl monosubstituted o-(alkynyl)styrenes gives rise to 1-α-methoxy or 1-α-hydroxybenzyl-1H-indenes in a diastereospecific way. In contrast with β,β-disubstitued o-(alkynyl)styrenes, the stereochemical outcome of the process, diastereospecific reactions,...
Article
Gold(III)-catalyzed cycloisomerization of α-bis(indol-3-yl)methyl alkynols selectively affords 1-(indol-3-yl)carbazoles, in a transformation that takes place through a selective 1,2-alkyl vs 1,2-vinyl migration step in the vinyl-gold intermediate generated from the initial 5-endo-spirocyclization. The reaction proceeds well with either tertiary or...
Article
Immobilized sterically demanding NHC-Au(I) complexes Silica-[(IPrR)Au]Cl and Silica-[(IAdPrR)Au]Cl are synthesized and characterized. These complexes are suitable catalysts in typical homogeneous Au(I) catalyzed alkyne reactions such as the hydration, hydroamination, hydroarylation or cycloisomerization. The results obtained with the immobilized ca...
Article
Pyrrolidines are central heterocyclic compounds with endless applications in organic synthesis, metal- and organocatalysis. In particular, their potential as ligands for first-row transition-metal catalysts has inspired a new method to access complex poly-heterocyclic pyrrolidines in one-step from available materials. This fundamental step forward...
Article
Pyrrolidines are important heterocyclic compounds with endless applications in organic synthesis, metal catalysis, and organocatalysis. Their potential as ligands for first-row transition-metal catalysts inspired a new method to access complex poly-heterocyclic pyrrolidines in one step from available materials. This fundamental step forward is base...
Article
A convenient procedure for accessing α,α-bis(indol-3-yl) ketones from indoles and α-oxoaldehydes is described using an inexpensive and commercially available catalyst such as p-toluenesulfonic acid monohydrate. This protocol allows for the first time the synthesis of 2,2-bis(indolyl)-1-alkylethanones by employing aliphatic 2-oxoaldehydes, even as a...
Article
Natural products are an abundant source of synthetic challenges that foster crucial breakthroughs in organic chemistry. Despite the superior complexity of these targets, ligand total synthesis can inspire solutions to unsolved chemical problems and provide access to creative catalyst designs. This Synpacts article presents a comparative analysis of...
Article
A rapid, scalable, and stereoselective assembly of multifunctional piperazines through a [3+3] coupling of azomethine ylides is developed.
Article
The development of more active C-H oxidation catalysts has inspired a rapid, scalable, and stereoselective assembly of multifunctional piperazines through a [3+3] coupling of azomethine ylides. A combination of visible-light irradiation and aluminum organometallics is essential to promote this transformation, which introduces visible-light photoche...
Article
The competition between π- and dual σ,π-gold-activation modes is revealed in the gold(I)-catalyzed heterocyclization of 1-(o-ethynylaryl)urea. A noticeable effect of various ligands in gold complexes on the choice of these activation modes is described. The cationic [Au(IPr)](+) (IPr=2,6-bis(diisopropylphenyl)imidazol-2-ylidene) complex cleanly pro...
Article
Selected examples from previous work on iodonium-triggered approaches for the functionalization of unsaturated systems, which summarize innovative transformations, are presented. This section is mostly focused on C-C bond-forming processes from alkynes that are directly bonded to relevant heteroatoms, such as iodine, silicon, or sulfur. Besides, re...
Article
Golden touch: N-allenylsulfonamides react with styrene derivatives to furnish chiral cyclobutanes in both high yield and enantioselectivity at -70 °C. Phosphoramidite ligands such as 1 facilitate this asymmetric gold(I)-catalyzed [2+2] cycloaddition. Tf=trifluoromethanesulfonyl.
Article
Ein Hauch von Gold: N‐Allenylsulfonamide reagieren bei −70 °C mit Styrolderivaten in hohen Ausbeuten und Enantioselektivitäten zu chiralen Cyclobutanen. Phosphoramidit‐Liganden wie 1 vermitteln diese asymmetrische Gold(I)‐katalysierte [2+2]‐Cycloaddition. Tf=Trifluormethansulfonyl.
Article
Intermolecular [2 + 2]-cycloaddition of allenes and alkenes substituted by electron-donor groups furnishes cyclobutane derivatives with complete stereoselectivity using low catalyst loading.
Article
Addition of catalytic amounts of a phosphite‐based gold(I) catalyst efficiently triggers the intermolecular [2+2] cycloaddition of allenes and alkenes substituted by electron‐donor groups. The reaction is fast and furnishes cyclobutane derivatives in a stereoselective manner using low catalyst loadings. Besides, the same catalyst selectively afford...
Article
The gold(I)-catalyzed cyclization reactions of N-(3-Iodoprop-2-ynyl)-N-tosylaniline derivatives afford iodinated 1,2-dihydroquinoline derivatives. Two regioisomer products are obtained, one derived from direct cyclization and other involving concomitant 1,2-iodo migration. The ratio of these two products can be modulated by a proper ancillary ligan...
Article
Doubling the bet: Two C[BOND]H bonds become functionalized upon exposure of ω-aryl propargylic tosylates to Sc(OTf)3 (see scheme). The reaction involves a new domino process that can tolerate both electron-withdrawing and -donating substituents on the arene unit. Different carbo- and heterocyclic frameworks can be assembled by using this approach t...
Article
Propargyl tosylates react with N-tosylaldimines to afford cyclopent-2-enimines in a gold-catalyzed process that involves a deep reorganization of both substrates. The formal [4 + 1] cyclization is initiated by a 1,2-migration of the tosylate that eventually generates a substituted 1,3-diene. Subsequent interaction with the imine launches a series o...

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