Jérôme Marrot

article

Accumulation, Characterization and Reactivity of Chiral Ammonium‐Carboxonium Dications in Superacid

Emanuela Berrino, Thomas Cantin, Maxime Artault, Stefanie Beck, more

Angewandte Chemie > 136 > 23 > n/a - n/a

The accumulation of chiral ammonium‐oxocarbenium dications in superacid is evidenced by low‐temperature NMR spectroscopy, X‐ray diffraction analysis and confirmed by DFT calculations. Its potential for the diastereoselective remote hydrofunctionalization of non‐activated alkene is also explored.

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Accumulation, Characterization and Reactivity of Chiral Ammonium‐Carboxonium Dications in Superacid

Emanuela Berrino, Thomas Cantin, Maxime Artault, Stefanie Beck, more

Angewandte Chemie International Edition > 63 > 23 > n/a - n/a

The accumulation of chiral ammonium‐oxocarbenium dications in superacid is evidenced by low‐temperature NMR spectroscopy, X‐ray diffraction analysis and confirmed by DFT calculations. Its potential for the diastereoselective remote hydrofunctionalization of non‐activated alkene is also explored.

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Perfluoroalkylated Sulfoximines as Analogues of Togni Reagents: The Crucial Role of Fluorine Atoms for the Stability of Hypervalent Iodine Scaffolds

Thibaut Duhail, Jorna Kalim, Jérôme Marrot, Bruce Pégot, more

European Journal of Organic Chemistry > 26 > 47 > n/a - n/a

Hypervalent iodine compounds are described with perfluoroalkyl chains and S‐perfluoromethyl sulfoximines as ligands of the halogen. The influence of these groups on the stability of the cyclic structure is studied. The crucial role of the trifluoromethyl chain is clearly highlighted as an efficient ligand for the hypervalency. The structure and the reactivity of the new skeletons are discussed in...

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Benzodithiazoles‐Sulfoximines: Preparation, Properties and Reactivities as Radical Perfluoroalkylating Agents

Thibaut Duhail, Samir Messaoudi, Guillaume Dagousset, Jérôme Marrot, more

Advanced Synthesis & Catalysis > 365 > 14 > 2392 - 2399

We describe the preparation of S‐perfluoroalkyl benzodithiazole trioxides as radical perfluoroalkylating reagents. Their syntheses were performed on a multi‐gram scale by an oxidative cyclization connecting the nitrogen of a sulfoximine and a sulfur atom previously introduced in the ortho position of this group. The structures and properties of these new molecules were carefully examined by X‐Ray...

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Organocatalyzed Synthesis of Tetrahydro‐α‐Carboline Derivatives Bearing N,O‐Acetals

Manon Genet, Abdelilah Takfaoui, Jérôme Marrot, Christine Greck, more

European Journal of Organic Chemistry > 2022 > 44 > n/a - n/a

An enantioselective organocatalytic reaction of indole‐derived‐1‐azadienes with aldehydes leading the formation of enantioenriched cyclic N,O‐acetals is reported. The corresponding products can be obtained with high levels of stereoselectivity (de >95 %, 65–99 % ee, 8–98 % yield). Furthermore, fused tetracyclic scaffolds can also be obtained by implementing a one‐pot strategy involving an additional...

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Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

Tanguy Jousselin‐Oba, Masashi Mamada, Karen Wright, Jérome Marrot, more

Angewandte Chemie > 134 > 1 > n/a - n/a

We report the synthesis and optoelectronic properties of TIPS‐peri‐pentacenopentacene (TIPS‐PPP), a vertical extension of TIPS‐pentacene (TIPS‐PEN) and a low‐band‐gap material with remarkable stability. We found the synthetic conditions to avoid the competition between 1,2‐ and 1,4‐addition of lithium acetylide on the large aromatic dione. The high stability of TIPS‐PPP is due to the peri‐fusion which...

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Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

Tanguy Jousselin‐Oba, Masashi Mamada, Karen Wright, Jérome Marrot, more

Angewandte Chemie International Edition > 61 > 1 > n/a - n/a

We report the synthesis and optoelectronic properties of TIPS‐peri‐pentacenopentacene (TIPS‐PPP), a vertical extension of TIPS‐pentacene (TIPS‐PEN) and a low‐band‐gap material with remarkable stability. We found the synthetic conditions to avoid the competition between 1,2‐ and 1,4‐addition of lithium acetylide on the large aromatic dione. The high stability of TIPS‐PPP is due to the peri‐fusion which...

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Host‐Guest Complexation Between Cyclodextrins and Hybrid Hexavanadates: What are the Driving Forces?

Ibrahima Fa Bamba, Clément Falaise, Jérôme Marrot, Patrick Atheba, more

Chemistry – A European Journal > 27 > 62 > 15516 - 15527

Host‐guest complexes between native cyclodextrins (α‐, β‐ and γ‐CD) and hybrid Lindqvist‐type polyoxovanadates (POVs) [V₆O₁₃((OCH₂)₃C−R)₂]^2– with R = CH₂CH₃, NO₂, CH₂OH and NH(BOC) (BOC = N‐tert‐butoxycarbonyl) were studied in aqueous solution. Six crystal structures determined by single‐crystal X‐ray diffraction analysis revealed the nature of the functional R group strongly influences the host–guest...

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Construction of Enantioenriched 4,5,6,7‐Tetrahydrofuro[2,3‐b]pyridines through a Multicatalytic Sequence Merging Gold and Amine Catalysis

Manon Genet, Abdelilah Takfaoui, Jérôme Marrot, Christine Greck, more

Advanced Synthesis & Catalysis > 363 > 19 > 4516 - 4520

A series of enantioenriched 4,5,6,7‐tetrahydrofuro[2,3‐b]pyridines were accessed by a cycloisomerization/cycloaddition strategy. Starting from ynamide derivatives and aldehydes, yields ranging from 27 to 90% and high levels of stereoselectivity (de>95%, 93–99% ee) were obtained through sequential relay catalysis. The concurrent use of a gold complex with a diphenylprolinol silyl ether was applied...

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Cover Picture: Construction of Enantioenriched 4,5,6,7‐Tetrahydrofuro[2,3‐b]pyridines through a Multicatalytic Sequence Merging Gold and Amine Catalysis (Adv. Synth. Catal. 19/2021)

Manon Genet, Abdelilah Takfaoui, Jérôme Marrot, Christine Greck, more

Advanced Synthesis & Catalysis > 363 > 19 > 4460 - 4460

The inside cover picture, designed by Fabrice Goursaud, holder of a PhD in organic chemistry and recently graduated from art school, illustrates the stereoselective synthesis of tetrahydro[2,3‐b]pyridine frameworks via one‐pot metal‐organo relay catalysis. The strategy, which involves a gold‐catalyzed cycloisomerization and a chiral amine mediated cycloaddition reaction, provides the targeted molecules...

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“Host in Host” Supramolecular Core–Shell Type Systems Based on Giant Ring‐Shaped Polyoxometalates

Clément Falaise, Soumaya Khlifi, Pierre Bauduin, Philipp Schmid, more

Angewandte Chemie International Edition > 60 > 25 > 14146 - 14153

Herein, we show how the chaotropic effect arising from reduced molybdate ions in acidified aqueous solution is able to amplify drastically weak supramolecular interactions. Time‐resolved Small Angle X‐ray Scattering (SAXS) analysis suggests that molybdenum‐blue oligomeric species form huge aggregates in the presence of γ‐cyclodextrin (γ‐CD) which results in the fast formation of nanoscopic {Mo₁₅₄}‐based...

article

“Host in Host” Supramolecular Core–Shell Type Systems Based on Giant Ring‐Shaped Polyoxometalates

Clément Falaise, Soumaya Khlifi, Pierre Bauduin, Philipp Schmid, more

Angewandte Chemie > 133 > 25 > 14265 - 14272

Herein, we show how the chaotropic effect arising from reduced molybdate ions in acidified aqueous solution is able to amplify drastically weak supramolecular interactions. Time‐resolved Small Angle X‐ray Scattering (SAXS) analysis suggests that molybdenum‐blue oligomeric species form huge aggregates in the presence of γ‐cyclodextrin (γ‐CD) which results in the fast formation of nanoscopic {Mo₁₅₄}‐based...

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Photoactive Organic/Inorganic Hybrid Materials with Nanosegregated Donor–Acceptor Arrays

Xiaolei Zhu, Cheriehan Hessin, Aude Salamé, Lydia Sosa‐Vargas, more

Angewandte Chemie International Edition > 60 > 15 > 8419 - 8424

The synthesis of the first mesogenic donor‐acceptor polyoxometalate (POM)‐based hybrid is herein described. The structural and electronic properties of the hybrid compound were evaluated through combination of small‐ and wide‐angle X‐ray scattering, optical microscopy, electrochemistry and photoluminescence. In the solid state, the compound behaves as a birefringent solid, displaying a lamellar organization...

article

Photoactive Organic/Inorganic Hybrid Materials with Nanosegregated Donor–Acceptor Arrays

Xiaolei Zhu, Cheriehan Hessin, Aude Salamé, Lydia Sosa‐Vargas, more

Angewandte Chemie > 133 > 15 > 8500 - 8505

The synthesis of the first mesogenic donor‐acceptor polyoxometalate (POM)‐based hybrid is herein described. The structural and electronic properties of the hybrid compound were evaluated through combination of small‐ and wide‐angle X‐ray scattering, optical microscopy, electrochemistry and photoluminescence. In the solid state, the compound behaves as a birefringent solid, displaying a lamellar organization...

article

Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids

Naresh Bhuma, Ludivine Lebedel, Hiroki Yamashita, Yutaka Shimizu, more

Angewandte Chemie > 133 > 4 > 2064 - 2069

The transformation of glycals into 2,3‐unsaturated glycosyl derivatives, reported by Ferrier in 1962, is supposed to involve an α,β unsaturated glycosyl cation, an elusive ionic species that has still to be observed experimentally. Herein, while combination of TfOH and flow conditions failed to observe this ionic species, its extended lifetime in superacid solutions allowed its characterization by...

article

Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids

Naresh Bhuma, Ludivine Lebedel, Hiroki Yamashita, Yutaka Shimizu, more

Angewandte Chemie International Edition > 60 > 4 > 2036 - 2041

The transformation of glycals into 2,3‐unsaturated glycosyl derivatives, reported by Ferrier in 1962, is supposed to involve an α,β unsaturated glycosyl cation, an elusive ionic species that has still to be observed experimentally. Herein, while combination of TfOH and flow conditions failed to observe this ionic species, its extended lifetime in superacid solutions allowed its characterization by...

article

Synthesis of S‐Trifluoromethyl S‐Arylsulfoximine Thioglycosides through Pd‐Catalyzed Migita Cross‐Coupling

Nedjwa Bennai, Nada Ibrahim, Jérôme Marrot, Mohamed Belkadi, more

European Journal of Organic Chemistry > 2020 > 31 > 4972 - 4981

A general protocol for the synthesis of S‐trifluoromethyl S‐arylsulfoximine thioglycosides has been reported. This protocol is based on a Pd‐catalyzed Migita cross‐coupling between o‐iodo S‐trifluoromethyl S‐arylsulfoximines and a broad range of 1‐thiosugars. This method gives access to a series of functionalized S‐trifluoromethyl S‐arylsulfoximine thioglycosides in moderate to good yields. Moreover,...

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A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4‐Dienals through an Interrupted iso‐Nazarov Reaction

Anne‐Sophie Marques, Thibaut Duhail, Jérome Marrot, Isabelle Chataigner, more

Angewandte Chemie > 131 > 29 > 10074 - 10078

We report an unprecedented domino polycyclization from readily available 2,4‐dienals and cyclic α,β‐unsaturated imines that is initiated by an iso‐Nazarov reaction. This Brønsted acid promoted reaction enables the concomitant formation of four bonds, three cycles, and four contiguous stereogenic centers to yield elaborated structures in a single operation. A range of fused hexacyclic molecules is...

article

A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4‐Dienals through an Interrupted iso‐Nazarov Reaction

Anne‐Sophie Marques, Thibaut Duhail, Jérome Marrot, Isabelle Chataigner, more

Angewandte Chemie International Edition > 58 > 29 > 9969 - 9973

We report an unprecedented domino polycyclization from readily available 2,4‐dienals and cyclic α,β‐unsaturated imines that is initiated by an iso‐Nazarov reaction. This Brønsted acid promoted reaction enables the concomitant formation of four bonds, three cycles, and four contiguous stereogenic centers to yield elaborated structures in a single operation. A range of fused hexacyclic molecules is...

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Evidence of Phosphonium‐Carbenium Dication Formation in a Superacid: Precursor to Fluorinated Phosphine Oxides

Ugo Castelli, Jean‐François Lohier, Ines Drukenmüller, Agnès Mingot, more

Angewandte Chemie > 131 > 5 > 1369 - 1374

Unambiguously confirmed by low‐temperature in situ NMR experiments, X‐ray diffraction and vibrational spectroscopy, phosphonium‐carbenium superelectrophiles are shown to be generated in strong acidic conditions. Representing crucial intermediates, their exploitation allows for the synthesis of unprecedented fluorinated (cyclic) phosphine oxides.

INFONA - science communication portal

Search results for: Jérôme Marrot

Accumulation, Characterization and Reactivity of Chiral Ammonium‐Carboxonium Dications in Superacid

Accumulation, Characterization and Reactivity of Chiral Ammonium‐Carboxonium Dications in Superacid

Perfluoroalkylated Sulfoximines as Analogues of Togni Reagents: The Crucial Role of Fluorine Atoms for the Stability of Hypervalent Iodine Scaffolds

Benzodithiazoles‐Sulfoximines: Preparation, Properties and Reactivities as Radical Perfluoroalkylating Agents

Organocatalyzed Synthesis of Tetrahydro‐α‐Carboline Derivatives Bearing N,O‐Acetals

Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

Host‐Guest Complexation Between Cyclodextrins and Hybrid Hexavanadates: What are the Driving Forces?

Construction of Enantioenriched 4,5,6,7‐Tetrahydrofuro[2,3‐b]pyridines through a Multicatalytic Sequence Merging Gold and Amine Catalysis

Cover Picture: Construction of Enantioenriched 4,5,6,7‐Tetrahydrofuro[2,3‐b]pyridines through a Multicatalytic Sequence Merging Gold and Amine Catalysis (Adv. Synth. Catal. 19/2021)

“Host in Host” Supramolecular Core–Shell Type Systems Based on Giant Ring‐Shaped Polyoxometalates

“Host in Host” Supramolecular Core–Shell Type Systems Based on Giant Ring‐Shaped Polyoxometalates

Photoactive Organic/Inorganic Hybrid Materials with Nanosegregated Donor–Acceptor Arrays

Photoactive Organic/Inorganic Hybrid Materials with Nanosegregated Donor–Acceptor Arrays

Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids

Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids

Synthesis of S‐Trifluoromethyl S‐Arylsulfoximine Thioglycosides through Pd‐Catalyzed Migita Cross‐Coupling

A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4‐Dienals through an Interrupted iso‐Nazarov Reaction

A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4‐Dienals through an Interrupted iso‐Nazarov Reaction

Evidence of Phosphonium‐Carbenium Dication Formation in a Superacid: Precursor to Fluorinated Phosphine Oxides

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