Convenient in situ generation of a chiral bis-N-heterocyclic carbene palladium catalyst and its application in enantioselective synthesis

Mullick, Amrita B.; Jeletic, Matthew S.; Powers, Andrew R.; Ghiviriga, Ion; Abboud, Khalil A.; Veige, Adam S.

doi:10.1016/j.poly.2012.07.046

Cited by 18 publications

(11 citation statements)

References 107 publications

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“…[I – ]‐ and [CF 3 SO 3 – ]‐based chiral DOSs 26 have also been prepared and used by Veige et al, to study enantioselective conjugate addition of arylboronic acids to cyclic enones (Scheme ) 50…”

Section: Applicationsmentioning

confidence: 99%

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

D’Anna¹,

Noto²

2014

Eur J Org Chem

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During recent years growing interest has been devoted to the synthesis and applications of polycationic organic salts. Among them, di‐ and tricationic organic salts can be considered the natural evolution of monocationic ones. These last have given rise to the large class of ionic liquids. In the cases of di‐ and tricationic organic salts, the potential to change their structural features simply by varying the properties either of the charged heads or of the spacers separating them provides the opportunity to obtain materials suitable for different applications. This review article highlights recent progress in the study of the properties of di‐ and tricationic organic salts, as well as in some of their uses as solvent systems, receptors for anion recognition, ionic liquid crystals, low‐molecular‐weight gelators, additives for dye‐sensitized solar cells, and so on.

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Section: Applicationsmentioning

confidence: 99%

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

D’Anna¹,

Noto²

2014

Eur J Org Chem

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“…We believe the catalytic system presented here can be a useful alternative method for achieving the asymmetric reduction of various aryl ketones under mild conditions. The efficient enantioselective hydrosilylation of ketones catalyzed by NHC–Ir catalysts generated in situ using highly tunable azolium NHC ligand precursors is the subject of ongoing research in our laboratory 18…”

Section: Discussionmentioning

confidence: 99%

Enantioselective Hydrosilylation of Ketones Catalyzed by a Readily Accessible N‐Heterocyclic Carbene–Ir Complex at Room Temperature

et al. 2014

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A series of functionalized azolium compounds were synthesized from chiral α‐amino acid derivatives such as β‐amino alcohols. Reaction of hydroxy‐amide‐functionalized azolium salts thus obtained with Ag2O afforded N‐heterocyclic carbene‐Ag (NHC–Ag) complexes. Subsequent treatment of the resulting silver compound with [IrCl(cod)]2 yielded monodentate IrCl(cod)(NHC), which was stable in air. The NHC–Ir complex facilitated efficient asymmetric hydrosilylation of ketones using (EtO)2MeSiH under ambient conditions. A chiral ligand containing an isobutyl stereodirecting group was found to be the best ligand for the functionalized NHC–Ir complexes that were examined. A linear relationship was found between the catalyst ee and the product ee. The hydroxy functional group on the NHC ligand side‐arm not only induced stereocontrol but also enhanced the reaction rate.

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“…In addition, the authors proposed a catalytic cycle for this reaction (Scheme 9). In 2013, the most recent NHC-Pd based system has been developed by Mullick et al who used ligands derived from trans-9,10-dihydro-9,10-ethanoanthracene-11,12-diyl (DEA) and trans-9,10-dihydro-9,10-ethanoanthracene-11,12-diylmethanediyl (DEAM) in form of Pd-bisNHC complexes [46]. The catalysts were prepared in situ and tested for the addition reaction of various boronic acids to five and six-membered enones (Table 16).…”

Section: Catalytic Systems Based On Nhc Ligandsmentioning

confidence: 99%

“…The results were unsatisfactory in terms of yield and enantioselectivity (24-98%; 30-51% ee) and most of the studied combinations gave no product or the authors were not able to determine the enantioselectivity. A selection of some interesting results is summarised in Table 16 [46]. Scheme 9: Proposed catalytic cycle for the addition of phenylboronic acids to 2-cyclohexenone catalysed by Pd-NHC complex PdL7b [44].…”

Section: Catalytic Systems Based On Nhc Ligandsmentioning

confidence: 99%

Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones

Bartáček¹,

Svoboda²,

Kocúrik³

et al. 2021

Beilstein J. Org. Chem.

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The transition metal (palladium)-catalysed asymmetric 1,4-addition of arylboronic acids to conjugated enones belong to the most important and emerging strategies for the construction of C–C bonds in an asymmetric fashion. This review covers known catalytic systems used for this transformation. For clarity, we are using the type of ligand as a sorting criterion. Finally, we attempted to create a flowchart facilitating the selection of a suitable ligand for a given combination of enone and arylboronic acid.

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Convenient in situ generation of a chiral bis-N-heterocyclic carbene palladium catalyst and its application in enantioselective synthesis

Cited by 18 publications

References 107 publications

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

Enantioselective Hydrosilylation of Ketones Catalyzed by a Readily Accessible N‐Heterocyclic Carbene–Ir Complex at Room Temperature

Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones

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