Synthesis and catalytic activity of a complex of 1,1´-bis-isoquinoline N,N´-dioxide with PdCl2

Bulygina, L. A.; Khrushcheva, N. S.; Sokolov, V. I.; Khodak, A. A.

doi:10.1007/s11172-015-0880-z

Cited by 3 publications

(4 citation statements)

References 10 publications

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“…Pyridine N ‐oxides, unlike their pyridine congeners, coordinate through hard oxygen atoms and therefore are not normally considered for use with soft metal ions, such as Pd(II), where “privileged” ligand architectures include N and/or P coordinating elements. Not least, this stems from a weak binding of neutral O ligands to metal resulting in an easy loss of the ligand, which in turn affects stereocontrol [23] . Most of the successful applications of chiral amine‐ N ‐oxides refer to complexes with harder metals, such as rare‐earth and early transition metals (including f‐block), [24] with only a handful of examples of late transition metals [25] .…”

Section: Resultsmentioning

confidence: 99%

“…Not least, this stems from a weak binding of neutral O ligands to metal resulting in an easy loss of the ligand, which in turn affects stereocontrol. [23] Most of the successful applications of chiral amine-N-oxides refer to complexes with harder metals, such as rare-earth and early transition metals (including f-block), [24] with only a handful of examples of late transition metals. [25] The selection of chiral N,N'-dioxides examined in this work is shown in Figure 1.…”

Section: Optimization Of the Reaction Conditionsmentioning

confidence: 99%

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Mechanistic Insight into Palladium‐Catalyzed Asymmetric Alkylation of Indoles with Diazoesters Employing Bipyridine‐N,N’‐dioxides as Chiral Controllers

Fukazawa,

Vaganov,

Burykina

et al. 2023

Adv Synth Catal

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Metal‐catalyzed asymmetric alkylation of indoles with α‐diazoesters is well‐known, however, the underlying mechanisms of this reaction, particularly the origin of stereoselectivity, remain uncertain. For the Pd catalysis, we address this cutting‐edge challenge from two complementary viewpoints – i) the molecular level regarding a single catalytically active Pd center; and ii) nano‐level Pd species investigating the factors favoring the appearance of the preferred catalytic centers. The formation of the active catalytic species was monitored by structural methods (NMR and ESI‐MS), and metal particles were characterized with electron microscopy (SEM, EDX). On the molecular level, chiral bipyridine‐N,N’‐dioxides proved to be competent chiral controllers. The kinetic and DFT computational data revealed a crucial role of water in the rate and selectivity determining steps and showed that the enantioselectivity of the process is controlled by the protodepalladation step. On the nano‐scale, the important effect of catalyst precursor on the overall reaction performance was shown.

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Section: Resultsmentioning

confidence: 99%

Section: Optimization Of the Reaction Conditionsmentioning

confidence: 99%

Mechanistic Insight into Palladium‐Catalyzed Asymmetric Alkylation of Indoles with Diazoesters Employing Bipyridine‐N,N’‐dioxides as Chiral Controllers

Fukazawa,

Vaganov,

Burykina

et al. 2023

Adv Synth Catal

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“…Resolved 1,1′-biisoquinoline N,N’ -dioxides have found some applications as enantioselective organic catalysts [ 49 , 50 , 97 , 98 , 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 ]. The complex (1,1′-biisoquinoline N,N’ -dioxide)dichloridopalladium is an effective catalyst for Suzuki cross-couplings and hydroxyarylation reactions [ 96 ].…”

Section: Synthesis Of 11′-biisoquinolinesmentioning

confidence: 99%

“…Both strategies are potentially of interest for future research in the field. 6a) are readily prepared from the parent 1,1biisoquinolines using classical methods of N-oxidation involving peracetic acid or MCPBA (MCPBA = 3-chloroperbenzoic acid) [47,48,96] and have been resolved using chiral HPLC. The compounds appear to be configurationally stable.…”

Section: Synthesis Of 11 -Biisoquinolinesmentioning

confidence: 99%

1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections

2021

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1,1′-Biisoquinolines are a class of bidentate nitrogen donor ligands in the heterocyclic diimine family. This review briefly discusses their properties and the key synthetic pathways available and then concentrates upon their coordination behaviour. The ligands are of interest as they exhibit the phenomenon of atropisomerism (hindered rotation about the C1–C1′ bond). A notation for depicting the stereochemistry in coordination compounds containing multiple stereogenic centers is developed. The consequences of the chirality within the ligand on the coordination behaviour is discussed in detail.

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Catalyst-free regio- and chemoselective addition of secondary phosphine oxides to isoquinolines

et al. 2020

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Synthesis and catalytic activity of a complex of 1,1´-bis-isoquinoline N,N´-dioxide with PdCl2

Cited by 3 publications

References 10 publications

Mechanistic Insight into Palladium‐Catalyzed Asymmetric Alkylation of Indoles with Diazoesters Employing Bipyridine‐N,N’‐dioxides as Chiral Controllers

Mechanistic Insight into Palladium‐Catalyzed Asymmetric Alkylation of Indoles with Diazoesters Employing Bipyridine‐N,N’‐dioxides as Chiral Controllers

1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections

Catalyst-free regio- and chemoselective addition of secondary phosphine oxides to isoquinolines

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