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@article{faucris.310462142,
abstract = {Dioxomolybdenum(VI) complexes (1-6) were prepared in good yields (≥79 %) using enantiopure C2 and C1-symmetric bidentate N,N-ligands (L1-L6) derived from (+)-camphor. The ligands and complexes were characterized by NMR spectroscopy, IR, and elemental analysis. Single crystal X-ray diffraction analyses of complexes 3, 4 and 6 confirmed the bidentate coordination modes of ligands L3, L4, and L6 and revealed distorted octahedral coordination geometries around the metal center. Complexes 3 and 6 form conformational isomers depending on the orientation of the substituents of the ligand aryl groups. Preliminary evaluation of the complexes as catalysts for the epoxidation of cyclohexene (81–93 % conversion) and cis-cyclooctene (66–94 % conversion) with cumyl hydroperoxide and 35 % w/w aqueous hydrogen peroxide (39–73 %) demonstrated their activity for oxygen atom transfer reactions, opening the way for asymmetric epoxidations.},
author = {Aguilera, Tania and Pastrán, Jesús and Llovera, Ligia and Linden, Anthony and Herrera, Alberto Cesar and Venuti, Doménico and Agrifoglio, Giuseppe and Dorta, Romano},
doi = {10.1002/zaac.202300104},
faupublication = {yes},
journal = {Zeitschrift für Anorganische und Allgemeine Chemie},
keywords = {(+)-camphor; bis-pyrazole; dioxomolybdenum(VI); enantiopure chiral ligands; epoxidation},
note = {CRIS-Team Scopus Importer:2023-09-15},
peerreviewed = {Yes},
title = {{C2} and {C1}-{Symmetric} {Camphopyrazole} {Dioxomolybdenum}({VI}) {Complexes} catalyze the {Epoxidation} of {Cyclic} {Olefins}},
year = {2023}
}
@article{faucris.204112220,
abstract = {Quinine-based (R)-tert-butylsulfinate 3 reacts with tris-lithiated bis-arylamide 2 to afford gram-quantities of optically pure (S*O)N(S*O) sulfoxide pincer ligand (R,R)-4. Deprotonation of (R,R)-4 and p-Tol-substituted analogue (S,S)-5 with MgPh2 and BnK yields respective Mg and K amido-bis-sulfoxides 6–9. In Mg complexes 6 and 7, the sulfoxide functions are O-coordinated, thereby imparting a pronounced helicity to the ligand backbone. Transmetalation of 6 and 7 with [PdCl2(NCPh)2] affords the S,S-coordinated C2-symmetric and the O,S-coordinated C1-symmetric chlorido complexes 10 and 11, respectively, and reaction of potassium amides 8 and 9 with [PdCl(CH3)(COD)] leads to methyl-palladium pincer complexes 12 and 13, respectively. The crystal structures of 6, 7, 12, and 13 reveal a chameleonic ligand system with predictable behavior: (R)-configured 4 induces pronounced λ backbone helicity in the O-coordinated Mg-complex and weaker δ helicity in S-coordinated Pd-complexes, while (S)-configured ligand 5 mirrors this stereochemistry. S-Coordination induces stronger, C2-symmetric, steric crowding in the head-on quadrants compared to O-coordination. When (R,R)-4 is reacted with 2 equiv of [Pd(CH3)2(tmeda)], crystalline chiral Pd-sulfenate complex 16 forms by elimination of iso-butene and methane with inversion of configuration at the sulfenate S ato},
author = {Seidel, Falk and Frieß, Sibylle and Heinemann, Frank Wilhelm and Chelouan, Ahmed and Scheurer, Andreas and Grasruck, Alexander and Herrera, Alberto Cesar and Dorta, Romano},
doi = {10.1021/acs.organomet.8b00038},
faupublication = {yes},
journal = {Organometallics},
pages = {1160-1171},
peerreviewed = {Yes},
title = {{C}-2-{Symmetric} ({SO}){N}({SO}) {Suloxide} {Pincer} {Complexes} of {Mg} and {Pd}: {Helicity} {Switch} by {Ambidentate} {S}/{O}-{Coordination} and {Isolation} of a {Chiral} {Pd}-{Sulfenate}},
volume = {37},
year = {2018}
}
@article{faucris.288289772,
abstract = {The new mono dibenzo[b,f]-azepinyl substituted P-alkene ligands 7-9, 20, and 21 were used to synthesize monomeric and dimeric Cu(i) complexes by using metal to ligand ratios of 2 : 1 and 1 : 1, respectively. With the super-bulky tris dibenzo[b,f]-azepinyl substituted P-alkenes 21, only monomers form with a 1 : 1 stoichiometry. Cationic complexes were obtained either by employing [Cu(OTf)](2)& BULL;C6H6 as the starting material, or by chloride abstractions from the monomeric chlorido complexes with NaB(Ar-F)(4) or TlBF4, whereas with silver salts only Ag(i)-P-alkene complexes were isolated by transmetallation. Chloride abstraction with NaB(Ar-F)(4) gave the 14 ve cationic complex 18, which shows no alkene coordination and a bent coordination geometry due to the steric pressure exerted by the ligand. The buried volumes of the ligands (calculated from X-ray diffraction data) increase in the order 8 < 7 < 9 < 20 < 21 with the last displaying a staggering V-bur of 60.6% (the crystallographic Tolman angle in copper complex 23 amounts to 229 & DEG;). The bulkiest ligand (21) allowed us to isolate and structurally characterize rare examples of 14 ve Cu(i) complexes, namely the neutral chloride 23 and, after salt metathesis with NaB(Ar-F)(4), the chlorido bridged dinuclear cation 26 exhibiting short Cu-Cl bonds.},
author = {Grasruck, Alexander and Parla, Giorgio and Heinemann, Frank Wilhelm and Langer, Jens and Herrera, Alberto Cesar and Friess, Stefan and Schmid, Guenter and Dorta, Romano},
doi = {10.1039/d2nj05222a},
faupublication = {yes},
journal = {New Journal of Chemistry},
note = {CRIS-Team WoS Importer:2023-01-27},
peerreviewed = {Yes},
title = {{Developing} bulky {P}-alkene ligands: stabilization of copper complexes with 14 valence electrons},
year = {2022}
}
@article{faucris.208916740,
author = {Chelouan, Ahmed and Bao, Siyuan and Frieß, Sibylle and Herrera, Alberto Cesar and Heinemann, Frank Wilhelm and Escalona, Ana and Grasruck, Alexander and Dorta, Romano},
doi = {10.1021/acs.organomet.8b00591},
faupublication = {yes},
journal = {Organometallics},
pages = {3983-3992},
peerreviewed = {Yes},
title = {{Developing} {Chiral} {Dibenzazepine}-{Based} {S}({O})-{Alkene} {Hybrid} {Ligands} for {Rh}({I}) {Complexation}: {Catalysts} for the {Base}-{Free} {Hayashi}-{Miyaura} {Reaction}},
volume = {37},
year = {2018}
}
@article{faucris.315102057,
abstract = {Alkene planar chirality is introduced in the ‘privileged’ P-alkene phosphoramidite ligand 1. The resulting diastereomeric ligands (pR,R)-5 and (pS,R)-5 form optically pure complexes of Rh(i) and Pd(ii), which catalyze conjugate additions of boron C-nucleophiles to enones and allylic alkylations, respectively. In the Rh-catalyzed reaction, the planar chirality of the alkene exerts absolute enantiocontrol over the potent BINOL auxiliary.},
author = {Leinauer, Luisa and Parla, Giorgio and Messelberger, Julian and Herrera, Alberto Cesar and Heinemann, Frank Wilhelm and Langer, Jens and Chuchelkin, Ilya and Grasruck, Alexander and Frieß, Sibylle and Chelouan, Ahmed and Gavrilov, Konstantin and Dorta, Romano},
doi = {10.1039/d3cc04972h},
faupublication = {yes},
journal = {Chemical Communications},
note = {CRIS-Team Scopus Importer:2023-12-15},
pages = {14451-14454},
peerreviewed = {Yes},
title = {{Evolution} of a ‘privileged’ {P}-alkene ligand: added planar chirality beats {BINOL} axial chirality in catalytic asymmetric {C}-{C} bond formation},
volume = {59},
year = {2023}
}
@article{faucris.268298970,
abstract = {Oxidative addition of 1.5 equiv of bromine or iodine to a Ir(I) sulfoxide pincer complex affords the corresponding Ir(IV) tris-bromido or tris-iodido complexes, respectively. The unprecedented trap-free reductive elimination of iodine from the Ir(IV)-iodido complex is induced by coordination of ligands or donor solvents. In the case of added I-, the isostructural tris-iodo Ir(III)-ate complex is quickly generated, which then can be readily reoxidized to the Ir(IV)-iodido complex with FcPF(6) or electrochemically. DFT calculations indicate an "inverted ligand field" in the Ir(IV) complexes and favor dinuclear pathways for the reductive elimination of iodine from the formal metal center.},
author = {Frieß, Sibylle and Benyak, Anna and Herrera, Alberto Cesar and Escalona Bauza, Ana Melissa and Heinemann, Frank Wilhelm and Langer, Jens and Fehn, Dominik and Pividori, Daniel Maximilian and Grasruck, Alexander and Munz, Dominik and Meyer, Karsten and Dorta, Romano},
doi = {10.1021/acs.inorgchem.1c02956},
faupublication = {yes},
journal = {Inorganic Chemistry},
month = {Jan},
note = {CRIS-Team WoS Importer:2022-01-21},
peerreviewed = {Yes},
title = {{Ir}({IV}) {Sulfoxide}-{Pincer} {Complexes} by {Three}-{Electron} {Oxidative} {Additions} of {Br}-2 and {I}-2. {Unprecedented} {Trap}-{Free} {Reductive} {Elimination} of {I}-2 from a formal d(5) {Metal}},
year = {2022}
}
@article{faucris.106916964,
abstract = {The 'privileged' P-alkene ligand (S)-2 is synthesized on a > 40 gram scale in 96% yield starting from dibenz[b, f] azepine-PCl2 (1; accessible on > 80 g scale) and (S)-BINOL. Similarly, the P-alkenes (R)-3 and the 'chiral-at-P' (S-P, S-C)-4 are obtained from (R)-Taddol [(R, R)-alpha, alpha, alpha', alpha'-tetraphenyl- 2,2-dimethyl-1,3-dioxolane-4,5-dimethanol] and (S)-alpha, alpha-diphenylprolinol, respectively, in multigram quantities and high purity. The crystal structures of (S-P, S-C)-4, its diastereomer (R-P, S-C)-4, and of the (R)-SPINOL-derived ligand (R)-5 are reported. A slightly revised synthesis of SPINOL is also disclosed.},
author = {Herrera, Alberto Cesar and Linden, Anthony and Heinemann, Frank Wilhelm and Brachvogel, Rene-Chris and von Delius, Max and Dorta, Romano},
doi = {10.1055/s-0035-1560410},
faupublication = {yes},
journal = {Synthesis-Stuttgart},
keywords = {synthetic methods;ligand synthesis;chiral ligands},
pages = {1117-1121},
peerreviewed = {Yes},
title = {{Optimized} {Syntheses} of {Optically} {Pure} {P}-{Alkene} {Ligands}: {Crystal} {Structures} of a {Pair} of {P}-{Stereogenic} {Diastereomers}},
volume = {48},
year = {2016}
}
@article{faucris.259298180,
abstract = {Ruthenium (II) piano-stool complexes with bis-(+)-camphopyrazole ligands of C2 and C1 symmetry were prepared in good yields (66–98%). New C2-C1 ligands and complexes were characterized by multinuclear NMR spectroscopy, FT-IR and elemental analysis. The catalytic performance of the Ru(II)-bis-(+)-camphopyrazole complexes in the transfer hydrogenation of benzaldehyde and valeraldehyde using isopropanol/potassium carbonate and formic acid/triethylamine mixtures as hydrogen donors, was evaluated, resulting in moderate yields (>54%) for the reduction to the desired primary alcohols. The system with isopropanol as hydrogen source proved to be more selective than the analogous system using the azeotropic formic acid/triethylamine mixture, allowing benzyl alcohol to be obtained in quantitative yield (>99%) for a particular catalyst precursor. Furthermore, complexes with C2 symmetry ligands showed higher yields than those with C1 symmetry ligands in all of the evaluated systems.},
author = {Blanco, Christian O. and Llovera, Ligia and Herrera, Alberto Cesar and Dorta, Romano and Agrifoglio, Giuseppe and Venuti, Doménico and Landaeta, Vanessa R. and Pastrán, Jesús},
doi = {10.1016/j.ica.2021.120429},
faupublication = {yes},
journal = {Inorganica Chimica Acta},
keywords = {Aldehydes; C; Ruthenium (II); Transfer hydrogenation},
note = {CRIS-Team Scopus Importer:2021-05-28},
peerreviewed = {Yes},
title = {{Ruthenium} ({II}) complexes with {C2}- and {C1}-symmetric bis-(+)-camphopyrazole ligands and their evaluation in catalytic transfer hydrogenation of aldehydes},
volume = {524},
year = {2021}
}
@article{faucris.208917672,
author = {Freitag, Benjamin and Elsen, Holger and Pahl, Jürgen and Ballmann, Gerd and Herrera, Alberto Cesar and Dorta, Romano and Harder, Sjoerd},
doi = {10.1021/acs.organomet.7b00200},
faupublication = {yes},
journal = {Organometallics},
pages = {1860-1866},
peerreviewed = {Yes},
title = {s-{Block} {Metal} {Dibenzoazepinate} {Complexes}: {Evidence} for {Mg}-{Alkene} {Encapsulation}},
volume = {36},
year = {2017}
}
@article{faucris.224621393,
abstract = {Dibenzazepinyl dichlorophosphine 2 reacts with (R,R)-2,3-O-isopropylidene-threitol (3) in Et2O solution to afford gram-quantities of the enantiopure macrocylic phosphoramidite (all-R)-6, which may be seen as a formal dimer of classic phosphoramidite P-alkene hybrid ligands. Complexation experiments with PdCl2 reveal highly selective formation of the trans-dinuclear complex (all-R)-11. The corresponding bulkier and rigidly trans-eclipsed 1,4-diol (S,S)-bis-hydroximethyl-9,10-dihydro-9,10-ethaneanthracene (4) does not favor macrocycle formation and exclusively leads to the new dibenzazepinyl phsophormaidite P-alkene ligand 7, which in Pd-catalyzed asymmetric allylic amination comes the well-known ‘privileged’ binol-derived P-alkene analogue 1 close in terms of enantioselection.},
author = {Frieß, Sibylle and Herrera, Alberto Cesar and Linden, Anthony and Heinemann, Frank Wilhelm and Dorta, Romano},
doi = {10.1016/j.jorganchem.2019.120876},
faupublication = {yes},
journal = {Journal of Organometallic Chemistry},
keywords = {Asymmetric allylic amination; Chiral macrocycle; Chiral P-alkene ligands; Hemilability; Phosphoramidites; trans-dinuclear palladium complex},
note = {CRIS-Team Scopus Importer:2019-08-16},
peerreviewed = {Yes},
title = {{Towards} enantiopure macrocyclic trans-dinucleating hemilabile {P}-{Alkene} ligands: {Syntheses}, structures, and {Chiral} {Pd}-{Complexes}},
volume = {898},
year = {2019}
}
@article{faucris.315103056,
abstract = {Cu(i)-Hydrido complexes supported by dibenzo[b,f]azepinyl P-alkene hybrid ligands and stabilized by electrostatic interactions in a Cu-H⋯KCl⋯BR3 arrangement can be trapped with CO2 at low temperature to afford Cu(i)-formates. The complexes are isolable with and without a pendant BEt3 group and show strong Cu-O and weak B-O interactions.},
author = {Grasruck, Alexander and Parla, Giorgio and Lou, Lisha and Langer, Jens and Neiß, Christian and Herrera, Alberto and Frieß, Sibylle and Görling, Andreas and Schmid, Günter and Dorta, Romano},
doi = {10.1039/d3cc03033d},
faupublication = {yes},
journal = {Chemical Communications},
note = {CRIS-Team Scopus Importer:2023-12-15},
pages = {13879-13882},
peerreviewed = {Yes},
title = {{Trapping} of soluble, {KCl}-stabilized {Cu}(i) hydrides with {CO2} gives crystalline formates},
volume = {59},
year = {2023}
}
@article{faucris.236863983,
abstract = {Deprotonation of phenyldibenzo[b,f]tropylidene (8) with LDA/t-BuOK followed by quenching with either diastereomer of inexpensive glucose-based t-Bu-sulfinate (R)- or (S)-11 affords a sulfoxide-alkene hybrid ligand as the diastereomeric pairs (SS,SC)-9/(SS,RC)-10 and (RS,RC)-9/(RS,SC)-10, respectively, which via chromatographic/recrystallization may be separated into the four isomers. The optically pure diastereomeric ligands (SS,SC)-9 and (SS,RC)-10 react with [RhCl(coe)2]2 to form the dinuclear complexes (RS,SC)-11 and (RS,RC)-12, respectively, in which the bidentate ligands coordinate the metal centers through the sulfur and alkene donor functions. These complexes catalyze the conjugate addition of arylboronic acids to cyclic Michael acceptors with enantioselectivities of up to 99% ee. DFT calculations show the preponderant influence of planar chirality of the ligand alkene function. The enantioselectivity switch observed between (RS,SC)-11 and (RS,RC)-12 is explained by the inverted cis-trans coordinations of the substrate molecules in catalytic steps.},
author = {Nikol, Alexander and Zhang, Ziyun and Chelouan, Ahmed and Falivene, Laura and Cavallo, Luigi and Herrera, Alberto and Heinemann, Frank Wilhelm and Escalona, Ana and Frieß, Sibylle and Grasruck, Alexander and Dorta, Romano},
doi = {10.1021/acs.organomet.0c00094},
faupublication = {yes},
journal = {Organometallics},
note = {CRIS-Team Scopus Importer:2020-04-03},
peerreviewed = {Yes},
title = {{Tricyclic} {Sulfoxide}-{Alkene} {Hybrid} {Ligands} for {Chiral} {Rh}({I}) {Complexes}: {The} "matched" {Diastereomer} {Catalyzes} {Asymmetric} {C}-{C} {Bond} {Formations}},
year = {2020}
}