Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis

Kazmaier, Uli; Alexakis, A.

doi:10.1007/978-3-642-22749-3

Cited by 109 publications

(2 citation statements)

References 83 publications

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“…P,N-ligands have been applied in a wide variety of chemical reactions ranging from hydrogenations [1–2] and allylic substitutions [3–4] to Heck reactions [5] and conjugate additions to enones [6]. Their popularity arises from the inherent electronic disparity of the phosphorus and the nitrogen donor groups, rendering one binding site a soft π-acceptor featuring a pronounced trans effect and the other site a hard σ-donor [7].…”

Section: Introductionmentioning

confidence: 99%

A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

Vasilenko¹,

Roth²,

Blasius³

et al. 2016

Beilstein J. Org. Chem.

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SummaryWe report the modular synthesis of three different types of neutral κ2-P,N-ligands comprising an imine and a phosphine binding site. These ligands were reacted with rhodium, iridium and palladium metal precursors and the structures of the resulting complexes were elucidated by means of X-ray crystallography. We observed that subtle changes of the ligand backbone have a significant influence on the binding geometry und coordination properties of these bidentate P,N-donors.

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Section: Introductionmentioning

confidence: 99%

A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

Vasilenko¹,

Roth²,

Blasius³

et al. 2016

Beilstein J. Org. Chem.

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“…Transition-metal-catalyzed allylic arylation reactions represents one of the most promising methods for the synthesis of allyl arenes (Scheme ). In most cases, the studies focused on the metal-catalyzed cross-coupling reactions of allyl electrophiles with aryl nucleophiles, such as organometallic reagents (Scheme A). For instance, the coupling reactions of allylic alcohol derivatives, such as allylic carboxylates, carbonates, phosphates, alcohols, or halides, with aryl-Grignard, -zinc, -boron reagents, etc .…”

mentioning

confidence: 99%

Photoredox/Nickel Dual-Catalyzed Regioselective Allylic Arylations of Allyl Trifluoroborates with Aryl Halides

Wang

Xie

et al. 2023

Org. Lett.

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An efficient photoredox/nickel dual-catalyzed coupling of allyl trifluoroborates with aryl halides has been developed, which provides an attractive route to diverse-substituted allylic benzenes. The method offers several advantages, such as high efficiency and regioselectivity, mild reaction conditions, wide substrate scope, and functional group compatibility. Mechanistic studies suggest that a π-allyl nickel(III) intermediate generated via the addition of an allyl radical to nickel species is possibly formed as a key reaction intermediate.

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Modern Catalytic Enantioselective Approaches to Piperidines

Sandmeier¹,

Carreira²

2020

Synthetic Approaches to Nonaromatic Nitrogen Heterocycles

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Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis

Cited by 109 publications

References 83 publications

A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

Photoredox/Nickel Dual-Catalyzed Regioselective Allylic Arylations of Allyl Trifluoroborates with Aryl Halides

Modern Catalytic Enantioselective Approaches to Piperidines

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